Document:

EX-10.2

 Exhibit 10.2 

EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (“Agreement”) is executed as of this 5th day of August, 2015 (“the Effective
Date”), by and between Stephanie Pugliese (“Executive”) and Duluth Holdings, Inc. (the “Company”). 

RECITALS 
 WHEREAS, the
Company desires to continue to employ Executive as its President and Chief Executive Officer, and Executive desires to be employed by the Company in such capacity, on the terms and conditions set forth herein. 

WHEREAS, as a result of Executive’s employment with the Company, Executive will have access to and be entrusted with valuable information
about the Company’s business and customers, including trade secrets and confidential information; and 
 WHEREAS, the Parties believe
it is in their best interests to make provision for certain aspects of their relationship during and after the period in which Executive is employed by the Company. 

NOW, THEREFORE, in consideration of the promises and the mutual agreements and covenants contained herein, and for other good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged by the Company and Executive (jointly, the “Parties”), the Parties agree as follows: 

ARTICLE I 
 EMPLOYMENT

 1.1 Position and Duties. Executive shall be employed in the positions of President and Chief Executive Officer of the Company
and shall be subject to the authority of, and shall report to, the Company’s Board of Directors (the “Board”). Executive’s duties and responsibilities shall include all those customarily attendant to the positions of
President and Chief Executive Officer, and such other duties and responsibilities as may be assigned from time-to-time by the Board. Executive shall devote Executive’s entire business time, attention, energies, and best efforts exclusively to
the business interests of the Company while employed by the Company, except as otherwise approved by the Board, to the extent that such activities do not impair Executive’s ability to perform Executive’s duties pursuant to this Agreement.
With respect to outside board activities, Executive, with the Board’s written approval (which approval shall not be unreasonably withheld), may serve on the board, advisory board or committee of: (a) any non-profit, charitable or similar
organization; and (b) following the second (2nd) anniversary of the Effective Date, one (1) for-profit organization. 

1.2 Term of Employment. The Company employs Executive, and Executive accepts employment by the Company, for the period commencing on
the Effective Date. Executive’s employment shall continue until terminated by the Company or Executive, in accordance with and subject to the termination provisions set forth in Article III, below (the “Employment Term”). Upon the
termination of Executive’s employment for any reason, Executive will be deemed to have resigned all of Executive’s positions with the Company and on its Board. 

 
Although the foregoing resignations are effective without any further action by Executive, Executive agrees to execute any documents reasonably requested by the Company to document such actions.

 1.3 Board Service. Executive will serve as a member of the Board until the earlier of the next annual meeting of the Company or
the termination of Executive’s employment with the Company for any reason. Thereafter, for so long as Executive remains President and Chief Executive Officer of the Company, Executive will be nominated to serve as a member of the Board.
Executive will be an employee director, and as such, Executive will not receive any additional compensation for serving as a member of the Board. 

ARTICLE II 
 COMPENSATION
AND OTHER BENEFITS 
 2.1 Base Salary. During the Employment Term, the Company shall pay Executive in substantially equal monthly
or more frequent installments, an annual salary of Three Hundred and Fifty Thousand Dollars ($350,000) (“Base Salary”), payable in accordance with the normal payroll practices and schedule of the Company. Executive’s Base
Salary shall be reviewed annually and may be increased at any time and from time-to-time as the Board and/or Compensation Committee of the Board (the “Compensation Committee”), as applicable, shall deem appropriate in its sole
discretion. Base Salary shall not be reduced at any time during the Employment Term, except with the consent of Executive. The term “Base Salary,” as utilized in this Agreement, shall refer to Base Salary as so increased or decreased. All
amounts in this Agreement are stated prior to deductions for federal and state income and employment tax withholding. 
 2.2 Incentive
Compensation. During the Employment Term, Executive shall be eligible to participate in annual incentive bonus plans (the “Bonus Plan”) offered by the Company to its senior executives from time-to-time. The performance metrics
for the Bonus Plan and the extent to which such metrics are met, as well as any other material terms, including threshold and maximum levels for annual cash incentive bonuses, shall be determined in the sole discretion of the Board and/or
Compensation Committee, as applicable. During the Employment Term, Executive will be eligible for grants of equity compensation awards offered to the Company’s management employees, in the sole discretion of the Board and/or Compensation
Committee, as applicable. 
 2.3 Other Benefits. 

(a) In General. During the Employment Term and subject to any limitation on participation provided by applicable law:
(i) Executive shall be entitled to participate in all applicable qualified and nonqualified retirement plans, practices, policies and programs of the Company; and (ii) Executive and/or Executive’s family, as the case may be, shall be
eligible for all applicable welfare benefit plans, practices, policies and programs provided by the Company, with respect to both (i) and (ii) above, to the same extent as other senior executives of the Company, other than severance plans,
practices, policies and programs. Nothing herein shall be deemed to limit the Company’s ability to amend, terminate or otherwise change any of the referenced plans, practices, policies and programs at any time, and from time-to-time. 

  
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 (b) Paid Time Off. During the Employment Term, Executive shall be entitled
to 208 hours of Paid Time Off per calendar year (pro-rated for partial years), which shall accrue in accordance with, and be otherwise subject to the provisions of the Company’s policy, as in effect from time-to-time. As used herein,
“Paid Time Off” means sick days, personal days and vacation days. 
 (c) Legal Fees. Executive shall
be entitled to reimbursement to Executive of all reasonable legal fees associated with the negotiation and drafting of this Agreement, provided that reimbursement of amounts under this Section 2.3(c) shall not exceed $5,000.00 in the aggregate.
Any reimbursement of such legal fees shall be paid within 60 days after Executive submits invoices therefor to the Company which comply with the Company’s reimbursement policy. 

2.4 Expense Reimbursement. The Company shall pay or reimburse Executive for all reasonable out-of-pocket expenses actually incurred by
Executive in the course of performing Executive’s duties for the Company in accordance with the Company’s reimbursement policies for senior executives as in effect from time-to-time. Executive shall keep accurate records and receipts of
such expenditures and shall submit such accounts and proof thereof as may from time-to-time be required in accordance with such expense account or reimbursement policies that the Company may establish for its senior executives generally. The
Company’s obligation to pay or reimburse Executive for certain expenses will comply with the requirements set forth in Section 1.409A-3(i)(1)(iv) of the regulations (the “409A Regulations”), promulgated under
Section 409A of the Code, including the requirement that the amount of expenses eligible for reimbursement during any calendar year may not affect the expenses eligible for reimbursement in any other taxable year. Further, reimbursement of
eligible expenses shall be made on or before the last day of the calendar year following the calendar year in which the expense was incurred, as required by Section 1.409A-3(i)(1)(iv) of the 409A Regulations. 

ARTICLE III 
 TERMINATION

 3.1 Right to Terminate; Automatic Termination. During the Employment Term, Executive’s employment may terminate for any
of the reasons set out in paragraphs (a) through (e) hereof. 
 (a) Termination by Death or Disability.
Executive’s employment and the Company’s obligations under this Agreement, except as provided in Section 3.2(a), below, shall terminate automatically, effective immediately and without any notice being necessary, upon Executive’s
death or a determination of Disability of Executive. For purposes of this Agreement, “Disability” means the inability of Executive to engage in any substantial gainful activity by reason of any medically determinable physical or
mental impairment which can be expected to result in death or can be expected to last for a continuous period of not less than 12 months, as determined by a physician selected by the Company and Executive. If the Company and Executive cannot agree
on a physician, 

  
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each party shall select a physician and the two physicians shall select a third who shall make the determination as to whether Executive has a condition that meets the definition of Disability.
Executive shall cooperate with any reasonable efforts to make such determination. In the event Executive is unable to select a physician, such selection shall be made by Executive’s spouse, and if Executive’s spouse is unable to select a
physician, such selection shall be made by Executive’s legal representative. Any such determination shall be conclusive and binding on the Parties. Any determination of Disability under this Section 3.1(a) is not intended to alter any
benefits any person and/or beneficiary may be entitled to receive under any long-term disability insurance policy carried by either the Company or Executive with respect to Executive, which benefits shall be governed solely by the terms of any such
insurance policy. 
 (b) Termination For Cause. The Company may terminate Executive’s employment and all of the
Company’s obligations under this Agreement, except as provided in Section 3.2(b), below, at any time for Cause (as defined below) by giving written notice to Executive stating the basis for such termination, effective immediately upon
giving such notice or at such other time thereafter as the Company may designate. “Cause” shall mean any of the following: (i) Executive has materially breached this Agreement, any other agreement to which Executive and the
Company are parties, or any Company policy, or has materially breached any other obligation or duty owed to the Company pursuant to law or the Company’s policies and procedures manual, including, but not limited to, Executive’s substantial
failure or willful refusal to perform Executive’s duties and responsibilities to the Company (other than as a result of Executive’s Death or Disability); (ii) Executive has committed an act of gross negligence, willful misconduct or
any violation of law in the performance of Executive’s duties for the Company; (iii) Executive has taken any action substantially likely to result in material discredit to or material loss of business, reputation or goodwill of the
Company; (iv) Executive has failed to follow resolutions that have been approved by a majority of the Board concerning the operations or business of the Company; (v) Executive has been convicted of or plead nolo contendere to a
felony or other crime, the circumstances of which substantially relate to Executive’s employment duties with the Company; provided however, that upon indictment in any such case, the Executive may, at the Company’s sole
discretion, be suspended without pay pending final resolution of the matter; (vi) Executive has misappropriated funds or property of the Company or engaged in any material act of dishonesty; or (vii) Executive has attempted to obtain a
personal profit from any transaction in which the Company has an interest, and which constitutes a corporate opportunity of the Company, or which is adverse to the interests of the Company, unless the transaction was approved in writing by the Board
after full disclosure of all details relating to such transaction. 
 (c) Termination by Resignation. Executive’s
employment and the Company’s obligations under this Agreement shall terminate automatically, except as provided in Section 3.2(b), below, when Executive voluntarily terminates Executive’s employment with the Company other than with
Good Reason (as described in Section 3.1(e), below), with ninety (90) days’ prior notice, or at such other earlier time as may be mutually agreed between the Parties following the provision of such notice. 

  
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 (d) Termination Without Cause. The Company may terminate Executive’s
employment and all of the Company’s obligations under this Agreement, except as provided in Section 3.2(c), below, at any time and for any reason. Such termination shall be effective immediately upon the Company providing notice to
Executive that Executive is terminated without Cause, or such other time thereafter as the Company shall designate. 
 (e)
Termination By Executive With Good Reason. Executive may terminate this Agreement with Good Reason, at which time Executive’s employment and all of the Company’s obligations under this Agreement shall terminate, except as provided
in Section 3.2(c). “Good Reason” shall mean the occurrence of any of the following conditions without Executive’s written consent, provided that Executive shall provide notice to the Company of the existence of the
condition within 90 days of the initial existence of such condition, the Company shall have 30 days from the date it receives the notice (the “Cure Period”) within which to cure such condition, and Executive must terminate
Executive’s employment within no more than 30 days after the expiration of the Cure Period if the Company does not cure the condition within the Cure Period: (i) a reduction in Executive’s title such that Executive is no longer
President and Chief Executive Officer of the Company; (ii) a material reduction in Executive’s then current level of Base Salary, except with the consent of Executive; (iii) a material diminution in Executive’s duties or
responsibilities; (iv) a breach by the Company of any material provision of this Agreement; or (v) the relocation of Executive’s office location more than twenty-five (25) miles from Belleville or Mt. Horeb, Wisconsin. 

3.2 Obligations Upon Termination. 

(a) Termination by Death or Disability. If Executive’s employment is terminated pursuant to Section 3.1(a),
above, Executive or Executive’s estate shall have no further rights against the Company hereunder, except for the right to receive: (i) any unpaid Base Salary with respect to the period prior to the effective date of termination of
employment; (ii) payment of any accrued but unused Paid Time Off, consistent with the Company’s policy related to carryovers of unused time and applicable law; (iii) all vested benefits to which Executive is entitled under any benefit
plans set forth in Section 2.3(a) hereof in accordance with the terms of such plans through the date employment terminates; (iv) reimbursement of expenses to which Executive may be entitled under Section 2.4 hereof (clauses
(i) through (iv) collectively, the “Accrued Obligations”); and (v) provided that Executive, or a representative of Executive’s estate, as the case may be, executes and delivers to the Company an
irrevocable release of all employment-related claims against the Company as further described in Section 3.2(c)(ii), a pro-rated annual incentive bonus payment (based on the number of days worked in that fiscal year) for the fiscal year in
which termination occurs based on actual performance-based bonus attainments for such fiscal year, payable in a lump sum. The pro-rated annual incentive bonus payment shall be made at such time as other participants in the plan receive their
payment, or, if later, on the sixtieth (60th) day following the date of Executive’s termination of employment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date. The treatment of
Executive’s equity awards, if any, shall be governed by the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to this Agreement. 

  
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 (b) Section 3.1(b)-(c) Terminations. If Executive’s
employment is terminated pursuant to Section 3.1(b) or (c), above, Executive shall have no further rights against the Company hereunder, except for the right to receive the Accrued Obligations. The treatment of Executive’s incentive
compensation provided under Section 2.2 hereof and the treatment of Executive’s equity awards, if any, shall be governed by the terms of the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to
this Agreement. 
 (c) Termination Without Cause or For Good Reason. 

(i) Company Obligations. If Executive’s employment is terminated pursuant to Section 3.1(d) or (e), above,
Executive shall have no further rights against the Company hereunder, except for the right to receive: (A) the Accrued Obligations; and (B) Severance Payments, as defined below, but only for so long as Executive complies with the
requirements of Articles IV, V, VI, VII, VIII, IX and X, below. For purposes of this Agreement, “Severance Payments” means: (1) twelve (12) months of Base Salary continuation; (2) a pro-rated annual incentive bonus
payment (based on the number of days worked in that fiscal year) for the fiscal year in which termination occurs based on actual performance-based bonus attainments for such fiscal year; (3) a historical bonus payment equal to the average
annual incentive compensation earned by Executive during the three most recent fiscal years of the Company prior to such termination (“Historical Bonus Payment”); and (4) to the extent it does not result in a tax or penalty on
the Company, reimbursement for that portion of the premiums paid by Executive to obtain COBRA continuation health coverage that equals the Company’s subsidy for health coverage for active employees with family coverage (if applicable) grossed
up so that Executive will be made whole for such premiums on an after-tax basis (“COBRA Continuation Payments”) for twelve (12) months following the date employment terminates (provided that Executive has not obtained health
coverage from any other source and is not eligible to receive health coverage from any other employer, in which event Executive shall no longer be entitled to reimbursement), at the times provided in subsection (iii), below. The treatment of
Executive’s equity awards, if any, shall be governed by the terms of the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to this Agreement. 

(ii) Release Requirement. Notwithstanding the foregoing, the Company shall not pay to Executive, and Executive shall not
have any right to receive, the Severance Payments unless, on or before the sixtieth (60th) day following the date of termination of employment: (A) Executive has executed and delivered to the Company a release of all employment-related
claims against the Company, its affiliates, successor companies, and their past and current directors, officers, employees and agents, in a form provided to Executive by the Company (which shall preserve, to the extent applicable, any indemnity
rights 

  
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Executive may be entitled to pursuant to Company by-laws, statute or any director and officer liability insurance maintained by the Company); and (B) the statutory revocation period for such
release has expired. 
 (iii) Timing of Payment of Severance Payments. Base Salary continuation shall commence on the
first payroll date following the expiration of the statutory revocation period, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date, and shall be paid over a twelve (12) month period in accordance
with the normal payroll practices and schedule of the Company. The pro-rated annual incentive bonus payment shall be made at such time as other participants in the plan receive their payment, or, if later, on the sixtieth (60th) day following the date of Executive’s termination of employment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date. The Historical Bonus
Payment shall be made in a lump sum on or before March 15 of the calendar year following the calendar year in which termination occurred, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date. The COBRA
Continuation Payments shall be paid on a monthly basis after Executive has paid the applicable COBRA premium payment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date, over a 12-month period.
Notwithstanding anything to the contrary contained in this Agreement, if: (A) Executive is a “specified employee” within the meaning of Section 1.409A-1(i) of the 409A Regulations; and
(B) the Severance Payments do not qualify for exemption from Section 409A under the short-term deferral exception to deferred compensation of Section 1.409A-1(b)(4) of the 409A Regulations, the separation pay plan exception to
deferred compensation of Section 1.409A-1(b)(9) of the 409A Regulations, or any other exception under the 409A Regulations, that portion of the Severance Payments not exempt from Section 409A of the Code shall be made in accordance
with the terms of this Agreement, but in no event earlier than the first to occur of: (1) the day after the six-month anniversary of Executive’s termination of employment; or (2) Executive’s death. Any payments delayed pursuant
to the prior sentence shall be made in a lump sum, on the first business day after the six-month anniversary of Executive’s termination of employment along with interest thereon payable at the short-term applicable federal rate for monthly
payments, as determined under Section 1274(d) of the Code, for the month in which Executive’s employment terminated. 

(iv) Treatment of Severance Payments for Tax and Benefit Purposes. The Severance Payments shall be treated as ordinary
income and shall be reduced by any applicable income or employment taxes which are required to be withheld under applicable law, and all amounts are stated before any such deduction. Furthermore, the Severance Payments shall not be included as
compensation for purposes of any qualified or nonqualified retirement or welfare benefit plan, program or policy of the Company. 

(d) Parachute Payments. Notwithstanding anything contained in this Agreement to the contrary, the Company, based on the
advice of its legal or tax counsel, 

  
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shall compute whether there would be any “excess parachute payments” payable to Executive, within the meaning of Section 280G of the Code, taking into account the total
‘‘parachute payments,” within the meaning of Section 280G of the Code, payable to Executive by the Company under this Agreement and any other plan, agreement or otherwise. If there would be any excess parachute payments, the
Company, based on the advice of its legal or tax counsel, shall compute the net after-tax proceeds related to such parachute payments, taking into account the excise tax imposed by Section 4999 of the Code, as if: (i) such parachute
payments were reduced, but not below zero, such that the total parachute payments payable to Executive would not exceed three (3) times the “base amount” as defined in Section 280G of the Code, less One Dollar ($1.00); or
(ii) the full amount of such parachute payments were not reduced. If reducing the amount of such parachute payments otherwise payable would result in a greater after-tax amount to Executive, such reduced amount shall be paid to Executive and
the remainder shall be forfeited. If not reducing such parachute payments otherwise payable would result in a greater after-tax amount to Executive, then such parachute payments shall not be reduced. If such parachute payments are reduced pursuant
to the foregoing, they will be reduced in the following order: first, by reducing any cash severance payments, then by reducing any fringe or other severance benefits, and finally by reducing any payments or benefits otherwise payable with respect
to, or measured by, the Company’s common stock (including without limitation by eliminating accelerated vesting, in each case starting with the installment or tranche last eligible to become vested absent the occurrence of a change in control).
Notwithstanding the foregoing, to the extent the Parties agree that any of the foregoing amounts are not parachute payments, such amounts shall not be reduced. To the extent the Parties cannot agree as to whether any of the payments are in fact
parachute payments, the Parties will designate, by mutual agreement, an unrelated third-party with tax expertise to make the determination. Notwithstanding any provision of this Section 3.2(d) to the contrary, no amount shall be subject to
reduction pursuant to this Section 3.2(d) to the extent the reduction would result in a violation of any applicable law. 
 ARTICLE
IV 
 CONFIDENTIALITY 

4.1 Confidentiality Obligations. 

(a) During Employment. Executive will not, during Executive’s employment with the Company, directly or indirectly
use or disclose any Confidential Information or Trade Secrets except in the interest and for the benefit of the Company. 

(b) Trade Secrets Post-Employment. After the end, for any reason, of Executive’s employment with the Company,
Executive will not directly or indirectly use or disclose any Trade Secrets. 
 (c) Confidential Information
Post-Employment. For a period of twenty-four (24) months following the end, for any reason, of Executive’s employment with the Company, Executive will not directly or indirectly use or disclose any Confidential Information. 

(d) Third Party Information. Executive further agrees not to use or disclose at any time information received by the
Company from others except in accordance with the Company’s contractual or other legal obligations. 

  
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 4.2 Definitions. 

(a) Trade Secret. The term “Trade Secret” has that meaning set forth under applicable law. 

(b) Confidential Information. The term “Confidential Information” means all non-Trade Secret
information of, about or related to the Company or provided to the Company by its customers and suppliers that is not known generally to the public or the Company’s competitors. Confidential Information includes, but is not limited to:
(i) strategic plans, budgets, forecasts, financial information, inventions, product designs and specifications, material specifications, materials sourcing information, product costs, information about products under development, research and
development information, production processes, equipment design and layout, customer lists, information about orders from and transactions with customers, sales and marketing information, strategies and plans, pricing information; and
(ii) information which is marked or otherwise designated or treated as confidential or proprietary by the Company. 

(c) Exclusions. Notwithstanding the foregoing, the terms “Confidential Information” and “Trade
Secret” do not include, and the obligations set forth in this Agreement do not apply to, any information which: (i) can be demonstrated by Executive to have been known by Executive prior to Executive’s employment by the Company;
(ii) is or becomes generally available to the public through no act or omission of Executive; (iii) is obtained by Executive in good faith from a third party who discloses such information to Executive on a non-confidential basis without
violating any obligation of confidentiality or secrecy relating to the information disclosed; or (iv) is independently developed by Executive outside the scope of Executive’s employment without use of Confidential Information or Trade
Secrets of the Company. 
 ARTICLE V 

NON-COMPETITION 
 5.1
Restrictions on Competition During Employment. During the term of Executive’s employment with the Company, Executive shall not directly or indirectly compete against the Company, or directly or indirectly divert or attempt to divert any
Customer’s business from the Company anywhere the Company does or is taking steps to do business. 
 5.2 Post-Employment Restricted
Services Obligation. For a period of two (2) years following the end, for whatever reason, of Executive’s employment with the Company, Executive agrees not to directly or indirectly provide Restricted Services to any Competitor in the
Territory. 

  
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 5.3 Definitions. 

(a) Restricted Services. The term “Restricted Services” means employment duties and functions of the
type provided by Executive to the Company during the twelve (12) month period immediately prior to the end, for whatever reason, of Executive’s employment with the Company. 

(b) Competitor. The term “Competitor” means Carhartt, Inc., L.L. Bean, Inc., Cabela’s Inc.,
Land’s End, Inc., VF Corporation, and any and all of their respective affiliates and successors. In addition, the term “Competitor” shall mean any corporation, partnership, association, or other person or entity that engages in any
business which, at any time during the eighteen (18) month period immediately prior to the end, for whatever reason, of Executive’s employment with the Company, and regardless of business format (including, but not limited to, department
stores, specialty stores, discount stores, direct marketing, or electronic commerce): (i) marketed, manufactured, or sold men’s or women’s work wear of the type marketed, manufactured or sold by the Company during the eighteen
(18) month period immediately prior to the end of Executive’s employment with the Company; and (ii) had combined annual revenues in excess of $100 million. 

(c) Territory. The term “Territory” shall mean the United States of America and Canada. 

ARTICLE VI 
 BUSINESS
IDEA RIGHTS 
 6.1 Assignment. The Company will own, and Executive hereby assigns to the Company and agrees to assign to the
Company, all rights in all Business Ideas which Executive originates or develops whether alone or working with others while Executive is employed by the Company. All Business Ideas which are or form the basis for copyrightable works are hereby
assigned to the Company and/or shall be assigned to the Company or shall be considered “works for hire” as that term is defined by United States Copyright Law. 

6.2 Definition of Business Ideas. The term “Business Ideas” means all ideas, designs, modifications, formulations,
specifications, concepts, know-how, trade secrets, discoveries, inventions, data, software, developments and copyrightable works, whether or not patentable or registrable, which Executive originates or develops, either alone or jointly with others
while Executive is employed by the Company and which are: (i) related to any business known to Executive to be engaged in or contemplated by the Company; (ii) originated or developed during Executive’s working hours; or
(iii) originated or developed in whole or in part using materials, labor, facilities or equipment furnished by the Company. 
 6.3
Disclosure. While employed by the Company, Executive will promptly disclose all Business Ideas to the Company. 
 6.4 Execution of
Documentation. Executive, at any time during or after the Employment Term, will promptly execute all documents which the Company may reasonably require to perfect its patent, copyright and other rights to such Business Ideas throughout the
world. 

  
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 ARTICLE VII 

NON-SOLICITATION OF EMPLOYEES 

During the term of Executive’s employment with the Company and for two (2) years thereafter, Executive shall not directly or
indirectly encourage any Company employee to terminate employment with the Company or solicit such an individual for employment outside the Company in any manner which would end or diminish that employee’s services to the Company. 

ARTICLE VIII 
 EMPLOYEE
DISCLOSURES AND ACKNOWLEDGMENTS 
 8.1 Confidential Information of Others. Executive warrants and represents to the Company that
Executive is not subject to any employment, consulting or services agreement, or any restrictive covenants or agreements of any type, which would conflict or prohibit Executive from fully carrying out Executive’s duties as described under the
terms of this Agreement. Further, Executive warrants and represents to the Company that Executive has not and will not retain or use, for the benefit of the Company, any confidential information, records, trade secrets, or other property of a former
employer. 
 8.2 Scope of Restrictions. Executive acknowledges that during the course of Executive’s employment with the
Company, Executive will gain knowledge of Confidential Information and Trade Secrets of the Company. Executive acknowledges that the Confidential Information and Trade Secrets of the Company are necessarily shared with Executive on a routine basis
in the course of performing Executive’s job duties and that the Company has a legitimate protectable interest in such Confidential Information and Trade Secrets, and in the goodwill and business prospects associated therewith. Executive
acknowledges that the Company does business in all states in the United States and in Canada. Accordingly, Executive acknowledges that the scope of the restrictions contained in this Agreement are appropriate, necessary and reasonable for the
protection of the business, goodwill and property rights of the Company, and that the restrictions imposed will not prevent Executive from earning a living in the event of, and after, the end, for any reason, of Executive’s employment with the
Company. 
 8.3 Prospective Employers. Executive agrees, during the term of any restriction contained in Articles IV, V, VI, VII,
VIII, IX and X of this Agreement, to disclose this Agreement to any entity which offers employment or engagement to Executive. Executive further agrees that, during the term of any restriction contained in Articles IV, V, VI, VII, VIII, IX and X,
the Company may send a copy of this Agreement to, or otherwise make the provisions hereof known to, any person or entity with which Executive seeks to establish a business relationship, including, without limitation, potential employers,
joint-venturers, or persons or entities to whom Executive seeks to provide consulting services as an independent contractor. 
 8.4 Third
Party Beneficiaries. All of the Company’s affiliates, successors and assigns are third party beneficiaries with respect to Executive’s performance of Executive’s duties under this Agreement and the undertakings and covenants
contained in this Agreement, and the Company and any such entity, enjoying the benefits thereof, may enforce this Agreement directly against Executive. 

  
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 8.5 Survival. The Covenants set forth in Articles IV, V, VI, VII, VIII, IX and X of this
Agreement shall survive the termination of this Agreement. 
 8.6 Injunctive Relief. Executive acknowledges that the services to be
rendered by Executive hereunder are of a special, unique, and extraordinary character and, in connection with such services, Executive will have access to Confidential Information and Trade Secrets that are vital to the Company’s business.
Executive consents and agrees that, in the event of the breach or a threatened breach by Executive of any of the provisions of this Agreement, the Company would sustain irreparable harm and that damages at law would not be an adequate remedy for a
violation of this Agreement, and, in addition to any other rights or remedies that the Company may have under this Agreement, common or statutory law or otherwise, the Company shall be entitled to specific performance and/or injunctive or other
equitable relief from a court of competent jurisdiction enforcing this Agreement and/or restraining Executive from committing, threatening to commit, or continuing any violation of this Agreement (in each case without posting a bond or other
security), including, but not limited to, restraining Executive from disclosing, using for any purpose, selling, transferring, or otherwise disposing of, in whole or in part, any Confidential Information and/or Trade Secrets. Nothing contained
herein shall be construed as prohibiting the Company from pursuing any other remedies available to it for any breach or threatened breach of any provision of this Agreement, including, but not limited to, the recovery of damages, costs, and fees,
including the recovery of any prior Severance Payments made to Executive. 
 8.7 Consistency With Applicable Law. Executive
acknowledges and agrees that nothing in this Agreement prohibits Executive from reporting possible violations of law to any governmental agency or entity or making other disclosures that are protected under the whistleblower provisions of federal,
state or local laws or regulations. 
 ARTICLE IX 

RETURN OF RECORDS 
 Upon
the end, for any reason, of Executive’s employment with the Company, or upon request by the Company at any time, Executive, within five (5) days after the termination of Executive’s employment or earlier upon the Company’s
written request, shall return to the Company all documents, records, information, equipment (including computers, laptops, tablet computers, cell phones and other such equipment (“Electronic Equipment”)) and materials belonging
and/or relating to the Company (except Executive’s own personnel and wage and benefit materials relating solely to Executive and Executive’s personal Electronic Equipment which is not owned by the Company), all passwords and/or access
codes related to such equipment and/or materials, and all copies of all such materials. Upon the end, for any reason, of Executive’s employment with the Company, or upon request of the Company at any time, Executive further agrees to destroy
such records maintained by Executive on Executive’s personally-owned Electronic Equipment, which destruction the Company may reasonably confirm. 

  
 12 

 ARTICLE X 

NONDISPARAGEMENT 

Executive agrees that Executive will not, at any time (whether during or after the Employment Term), publish or communicate to any person or
entity any Disparaging (as defined below) remarks, comments or statements concerning the Company and its respective present and former members, partners, directors, officers, shareholders, employees, agents, attorneys, successors and assigns, except
as required by law, rule or regulation. “Disparaging” remarks, comments or statements are those that impugn the character, honesty, integrity or morality or business acumen or abilities in connection with any aspect of the operation
of business of the individual or entity being disparaged. 
 ARTICLE XI 

MISCELLANEOUS 
 11.1
Notice. Notices and all other communications provided for in this Agreement shall be in writing and shall be delivered personally or sent by registered or certified mail, return receipt requested, postage prepaid, or sent by electronic mail
or prepaid overnight courier to the Parties at the addresses set forth below (or such other address as shall be specified by the Parties by like notice pursuant to this Section 11.1): 

 

							
	To the Company:	  	Duluth Holdings, Inc.	  	
		  	[Personal Information Omitted]	  	
			
	With a copy to:	  	Godfrey & Kahn, S.C.	  	
		  	[Personal Information Omitted]	  	
			
	To Executive:	  	Stephanie Pugliese	  	
		  	[Personal Information Omitted]	  	

 Such notices and communications shall be deemed given upon personal delivery or receipt at the address or email account of the
party stated above or at any other address specified by such party to the other party in writing, except that if delivery is refused or cannot be made for any reason, then such notice shall be deemed given on the third day after it is sent. 

11.2 Entire Agreement; Amendment; Waiver. This Agreement (including any documents referred to herein) sets forth the entire
understanding of the Parties hereto with respect to the subject matter contemplated hereby. Any and all previous agreements and 

  
 13 

 
understandings between or among the Parties regarding the subject matter hereof, whether written or oral, are superseded by this Agreement. This Agreement shall not be amended or modified except
by a written instrument duly executed by each of the Parties hereto. Any extension or waiver by any party of any provision hereto shall be valid only if set forth in an instrument in writing signed on behalf of such party. 

11.3 Headings. The headings of sections and paragraphs of this Agreement are for convenience of reference only and shall not control or
affect the meaning or construction of any of its provisions. 
 11.4 Attorneys’ Fees; Expenses. Except as provided in
Section 2.3(c), above, each party hereto shall bear and pay all of the respective fees, expenses and disbursements of their agents, representatives, accountants and counsel incurred in connection with and related to this Agreement. 

11.5 Waiver of Breach. The waiver by either party of the breach of any provision of this Agreement shall not operate or be construed as
a waiver of any subsequent breach by either party. 
 11.6 Severability. If any court of competent jurisdiction determines that any
provision of this Agreement is invalid or unenforceable, then such invalidity or unenforceability shall have no effect on the other provisions hereof, which shall remain valid, binding and enforceable and in full force and effect, and, to the extent
allowed by law, such invalid or unenforceable provision shall be construed in a manner so as to give the maximum valid and enforceable effect to the intent of the Parties expressed therein. 

11.7 Governing Law. This Agreement shall in all respects be construed according to the laws of the State of Wisconsin, without regard
to its conflict of laws principles. 
 11.8 Future Cooperation. Executive agrees that, during Executive’s employment and
following the termination of Executive’s employment for any reason, Executive will cooperate with requests by the Company to assist in the defense or prosecution of any lawsuits or claims in which the Company, or its officers, directors or
employees may be or become involved and in connection with any internal investigation or administrative, regulatory or judicial proceeding, in each case which relates to matters occurring while Executive was employed by the Company, at such times
and at such places as shall be mutually convenient for Executive and the Company, taking into account any employment commitments which Executive then has. Executive shall be compensated by the Company at a rate comparable to that which Executive
earned while an employee of the Company or that which Executive is currently earning, whichever is greater; provided, however, that during such time as Executive is receiving Severance Payments pursuant to Section 3.2(c) of this Agreement, such
Severance Payments shall be the sole compensation provided to Executive for services reasonably requested under this Section 11.8. 

11.9 Compliance with Section 409A of the Code and the 409A Regulations. This Agreement, and any ambiguity hereunder, shall be
interpreted and administered so that any payments or benefits are either exempt from or avoid taxation under Section 409A of the Code, the 409A Regulations and any authority promulgated thereunder. Executive acknowledges that

  
 14 

 
the Company has made no representations as to the treatment of the compensation and benefits provided hereunder and the Executive has been advised to obtain Executive’s own tax advice. Any
term used in this Agreement which is defined in Code Section 409A or the 409A Regulations shall have the meaning set forth therein unless otherwise specifically defined herein. Any obligations under this Agreement that are subject to the
requirements of Code Section 409A and arise in connection with Executive’s “termination of employment”, “termination” or other similar references shall only be triggered if the termination of employment or termination
qualifies as a “separation from service” within the meaning of Section 1.409A-1(h) of the 409A Regulations. Notwithstanding any other provision of this Agreement, if at the time of the termination of Executive’s employment,
Executive is a “specified employee,” as defined in Section 409A or the 409A Regulations, and any payments upon such termination under this Agreement hereof will result in additional tax or interest to Executive under Code
Section 409A, Executive will not be entitled to receive such payments until the date which is the earlier of: (i) six (6) months after the termination of Executive’s employment; or (ii) Executive’s death. Each amount or
benefit payable pursuant to this Agreement shall be deemed a separate payment for purposes of Section 409A and the 409A Regulations. 

11.10 Successors. 

(a) This Agreement is personal to Executive and shall not be assignable by Executive otherwise than by will or the laws of
descent and distribution. This Agreement shall inure to the benefit of and be enforceable by Executive’s legal representatives. 

(b) This Agreement shall be assignable by the Company without the written consent of Executive and shall inure to the benefit
of and be binding upon the Company and its respective successors and assigns. Upon assignment of this Agreement by the Company, all references to the “Company” shall be deemed to refer to the party to which this Agreement is assigned. 

11.11 Acknowledgement of Representation. Executive and the Company acknowledge that they have had the opportunity to be represented by
counsel of their own choosing and, therefore, in the event of a dispute over the meaning of this Agreement or any provisions thereof, neither party shall be entitled to any presumption of correctness in favor of the interpretation advanced by such
party or against the interpretation advanced by the other party. 
 IN WITNESS WHEREOF, the Parties hereto have caused this Agreement to be
duly executed as of the date first written above. 
  

	
	EXECUTIVE:
	
	 /s/ Stephanie Pugliese

	Stephanie Pugliese
	
	DULUTH HOLDINGS, INC.:
	
	 /s/ Stephen L. Schlecht

	Stephen L. Schlecht
	Executive Chairman

  
 15EX-10.3

 Exhibit 10.3 

EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (“Agreement”) is executed as of this 5th day of August, 2015 (“the Effective
Date”), by and between Mark DeOrio (“Executive”) and Duluth Holdings, Inc. (the “Company”). 

RECITALS 
 WHEREAS, the
Company desires to continue to employ Executive as its Senior Vice President and Chief Financial Officer, and Executive desires to be employed by the Company in such capacity, on the terms and conditions set forth herein. 

WHEREAS, as a result of Executive’s employment with the Company, Executive will have access to and be entrusted with valuable information
about the Company’s business and customers, including trade secrets and confidential information; and 
 WHEREAS, the Parties believe
it is in their best interests to make provision for certain aspects of their relationship during and after the period in which Executive is employed by the Company. 

NOW, THEREFORE, in consideration of the promises and the mutual agreements and covenants contained herein, and for other good and valuable
consideration, the receipt and sufficiency of which is hereby acknowledged by the Company and Executive (jointly, the “Parties”), the Parties agree as follows: 

ARTICLE I 
 EMPLOYMENT

 1.1 Position and Duties. Executive shall be employed in the positions of Senior Vice President and Chief Financial Officer of
the Company and shall be subject to the authority of, and shall report to, the Company’s Board of Directors (the “Board”). Executive’s duties and responsibilities shall include all those customarily attendant to the
positions of Senior Vice President and Chief Financial Officer, and such other duties and responsibilities as may be assigned from time-to-time by the Board. Executive shall devote Executive’s entire business time, attention, energies, and best
efforts exclusively to the business interests of the Company while employed by the Company, except as otherwise approved by the Board, to the extent that such activities do not impair Executive’s ability to perform Executive’s duties
pursuant to this Agreement. With respect to outside board activities, Executive, with the Board’s written approval (which approval shall not be unreasonably withheld), may serve on the board, advisory board or committee of: (a) any
non-profit, charitable or similar organization; and (b) following the second (2nd) anniversary of the Effective Date, one (1) for-profit organization. 

1.2 Term of Employment. The Company employs Executive, and Executive accepts employment by the Company, for the period commencing on
the Effective Date. Executive’s employment shall continue until terminated by the Company or Executive, in accordance with and subject to the termination provisions set forth in Article III, below (the “Employment Term”). Upon the
termination of Executive’s employment for any reason, Executive will be deemed to have resigned all of Executive’s positions with the Company. Although the foregoing resignations are effective without any further action by Executive,
Executive agrees to execute any documents reasonably requested by the Company to document such actions. 

 ARTICLE II 

COMPENSATION AND OTHER BENEFITS 

2.1 Base Salary. During the Employment Term, the Company shall pay Executive in substantially equal monthly or more frequent
installments, an annual salary of Two Hundred and Sixty Thousand Dollars ($260,000) (“Base Salary”), payable in accordance with the normal payroll practices and schedule of the Company. Executive’s Base Salary shall be reviewed
annually and may be increased at any time and from time-to-time as the Board and/or Compensation Committee of the Board (the “Compensation Committee”), as applicable, shall deem appropriate in its sole discretion. Base Salary shall
not be reduced at any time during the Employment Term, except with the consent of Executive. The term “Base Salary,” as utilized in this Agreement, shall refer to Base Salary as so increased or decreased. All amounts in this Agreement are
stated prior to deductions for federal and state income and employment tax withholding. 
 2.2 Incentive Compensation. During the
Employment Term, Executive shall be eligible to participate in annual incentive bonus plans (the “Bonus Plan”) offered by the Company to its senior executives from time-to-time. The performance metrics for the Bonus Plan and the
extent to which such metrics are met, as well as any other material terms, including threshold and maximum levels for annual cash incentive bonuses, shall be determined in the sole discretion of the Board and/or Compensation Committee, as
applicable. During the Employment Term, Executive will be eligible for grants of equity compensation awards offered to the Company’s management employees, in the sole discretion of the Board and/or Compensation Committee, as applicable. 

2.3 Other Benefits. 

(a) In General. During the Employment Term and subject to any limitation on participation provided by applicable law:
(i) Executive shall be entitled to participate in all applicable qualified and nonqualified retirement plans, practices, policies and programs of the Company; and (ii) Executive and/or Executive’s family, as the case may be, shall be
eligible for all applicable welfare benefit plans, practices, policies and programs provided by the Company, with respect to both (i) and (ii) above, to the same extent as other senior executives of the Company, other than severance plans,
practices, policies and programs. Nothing herein shall be deemed to limit the Company’s ability to amend, terminate or otherwise change any of the referenced plans, practices, policies and programs at any time, and from time-to-time. 

(b) Paid Time Off. During the Employment Term, Executive shall be entitled to 208 hours of Paid Time Off per calendar
year (pro-rated for partial years), which shall accrue in accordance with, and be otherwise subject to the provisions of the Company’s policy, as in effect from time-to-time. As used herein, “Paid Time Off” means sick days,
personal days and vacation days. 
 (c) Legal Fees. Executive shall be entitled to reimbursement to Executive of all
reasonable legal fees associated with the negotiation and drafting of this Agreement, provided that reimbursement of amounts under this Section 2.3(c) shall not exceed $5,000.00 in the aggregate. Any reimbursement of such legal fees shall be
paid within 60 days after Executive submits invoices therefor to the Company which comply with the Company’s reimbursement policy. 

  
 2 

 2.4 Expense Reimbursement. The Company shall pay or reimburse Executive for all reasonable
out-of-pocket expenses actually incurred by Executive in the course of performing Executive’s duties for the Company in accordance with the Company’s reimbursement policies for senior executives as in effect from time-to-time. Executive
shall keep accurate records and receipts of such expenditures and shall submit such accounts and proof thereof as may from time-to-time be required in accordance with such expense account or reimbursement policies that the Company may establish for
its senior executives generally. The Company’s obligation to pay or reimburse Executive for certain expenses will comply with the requirements set forth in Section 1.409A-3(i)(1)(iv) of the regulations (the “409A
Regulations”), promulgated under Section 409A of the Code, including the requirement that the amount of expenses eligible for reimbursement during any calendar year may not affect the expenses eligible for reimbursement in any other
taxable year. Further, reimbursement of eligible expenses shall be made on or before the last day of the calendar year following the calendar year in which the expense was incurred, as required by Section 1.409A-3(i)(1)(iv) of the 409A
Regulations. 
 ARTICLE III 

TERMINATION 
 3.1 Right
to Terminate; Automatic Termination. During the Employment Term, Executive’s employment may terminate for any of the reasons set out in paragraphs (a) through (e) hereof. 

(a) Termination by Death or Disability. Executive’s employment and the Company’s obligations under this
Agreement, except as provided in Section 3.2(a), below, shall terminate automatically, effective immediately and without any notice being necessary, upon Executive’s death or a determination of Disability of Executive. For purposes of this
Agreement, “Disability” means the inability of Executive to engage in any substantial gainful activity by reason of any medically determinable physical or mental impairment which can be expected to result in death or can be expected
to last for a continuous period of not less than 12 months, as determined by a physician selected by the Company and Executive. If the Company and Executive cannot agree on a physician, each party shall select a physician and the two physicians
shall select a third who shall make the determination as to whether Executive has a condition that meets the definition of Disability. Executive shall cooperate with any reasonable efforts to make such determination. In the event Executive is unable
to select a physician, such selection shall be made by Executive’s spouse, and if Executive’s spouse is unable to select a physician, such selection shall be made by Executive’s legal representative. Any such determination shall be
conclusive and binding on the Parties. Any determination of Disability under this Section 3.1(a) is not intended to alter any benefits any person and/or beneficiary may be entitled to receive under any long-term disability insurance policy
carried by either the Company or Executive with respect to Executive, which benefits shall be governed solely by the terms of any such insurance policy. 

  
 3 

 (b) Termination For Cause. The Company may terminate Executive’s
employment and all of the Company’s obligations under this Agreement, except as provided in Section 3.2(b), below, at any time for Cause (as defined below) by giving written notice to Executive stating the basis for such termination,
effective immediately upon giving such notice or at such other time thereafter as the Company may designate. “Cause” shall mean any of the following: (i) Executive has materially breached this Agreement, any other agreement to
which Executive and the Company are parties, or any Company policy, or has materially breached any other obligation or duty owed to the Company pursuant to law or the Company’s policies and procedures manual, including, but not limited to,
Executive’s substantial failure or willful refusal to perform Executive’s duties and responsibilities to the Company (other than as a result of Executive’s Death or Disability); (ii) Executive has committed an act of gross
negligence, willful misconduct or any violation of law in the performance of Executive’s duties for the Company; (iii) Executive has taken any action substantially likely to result in material discredit to or material loss of business,
reputation or goodwill of the Company; (iv) Executive has failed to follow resolutions that have been approved by a majority of the Board concerning the operations or business of the Company; (v) Executive has been convicted of or plead
nolo contendere to a felony or other crime, the circumstances of which substantially relate to Executive’s employment duties with the Company; provided however, that upon indictment in any such case, the Executive may, at
the Company’s sole discretion, be suspended without pay pending final resolution of the matter; (vi) Executive has misappropriated funds or property of the Company or engaged in any material act of dishonesty; or (vii) Executive has
attempted to obtain a personal profit from any transaction in which the Company has an interest, and which constitutes a corporate opportunity of the Company, or which is adverse to the interests of the Company, unless the transaction was approved
in writing by the Board after full disclosure of all details relating to such transaction. 
 (c) Termination by
Resignation. Executive’s employment and the Company’s obligations under this Agreement shall terminate automatically, except as provided in Section 3.2(b), below, when Executive voluntarily terminates Executive’s employment
with the Company other than with Good Reason (as described in Section 3.1(e), below), with ninety (90) days’ prior notice, or at such other earlier time as may be mutually agreed between the Parties following the provision of such
notice. 
 (d) Termination Without Cause. The Company may terminate Executive’s employment and all of the
Company’s obligations under this Agreement, except as provided in Section 3.2(c), below, at any time and for any reason. Such termination shall be effective immediately upon the Company providing notice to Executive that Executive is
terminated without Cause, or such other time thereafter as the Company shall designate. 
 (e) Termination By Executive
With Good Reason. Executive may terminate this Agreement with Good Reason, at which time Executive’s employment and all of the 

  
 4 

 
Company’s obligations under this Agreement shall terminate, except as provided in Section 3.2(c). “Good Reason” shall mean the occurrence of any of the following
conditions without Executive’s written consent, provided that Executive shall provide notice to the Company of the existence of the condition within 90 days of the initial existence of such condition, the Company shall have 30 days from the
date it receives the notice (the “Cure Period”) within which to cure such condition, and Executive must terminate Executive’s employment within no more than 30 days after the expiration of the Cure Period if the Company does
not cure the condition within the Cure Period: (i) a reduction in Executive’s title such that Executive is no longer Senior Vice President and Chief Financial officer of the Company; (ii) a material reduction in Executive’s
then current level of Base Salary, except with the consent of Executive; (iii) a material diminution in Executive’s duties or responsibilities; (iv) a breach by the Company of any material provision of this Agreement; or (v) the
relocation of Executive’s office location more than twenty five (25) miles from Belleville or Mt. Horeb, Wisconsin. 
 3.2
Obligations Upon Termination. 
 (a) Termination by Death or Disability. If Executive’s employment is
terminated pursuant to Section 3.1(a), above, Executive or Executive’s estate shall have no further rights against the Company hereunder, except for the right to receive: (i) any unpaid Base Salary with respect to the period prior to
the effective date of termination of employment; (ii) payment of any accrued but unused Paid Time Off, consistent with the Company’s policy related to carryovers of unused time and applicable law; (iii) all vested benefits to which
Executive is entitled under any benefit plans set forth in Section 2.3(a) hereof in accordance with the terms of such plans through the date employment terminates; (iv) reimbursement of expenses to which Executive may be entitled under
Section 2.4 hereof (clauses (i) through (iv) collectively, the “Accrued Obligations”); and (v) provided that Executive, or a representative of Executive’s estate, as the case may be, executes and
delivers to the Company an irrevocable release of all employment-related claims against the Company as further described in Section 3.2(c)(ii), a pro-rated annual incentive bonus payment (based on the number of days worked in that fiscal year)
for the fiscal year in which termination occurs based on actual performance-based bonus attainments for such fiscal year, payable in a lump sum. The pro-rated annual incentive bonus payment shall be made at such time as other participants in the
plan receive their payment, or, if later, on the sixtieth (60th) day following the date of Executive’s termination of employment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date. The
treatment of Executive’s equity awards, if any, shall be governed by the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to this Agreement. 

(b) Section 3.1(b)-(c) Terminations. If Executive’s employment is terminated pursuant to
Section 3.1(b) or (c), above, Executive shall have no further rights against the Company hereunder, except for the right to receive the Accrued Obligations. The treatment of Executive’s incentive compensation provided under
Section 2.2 hereof and the treatment of Executive’s equity awards, if any, shall be governed by the terms of the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to this Agreement. 

  
 5 

 (c) Termination Without Cause or For Good Reason. 

(i) Company Obligations. If Executive’s employment is terminated pursuant to Section 3.1(d) or (e), above,
Executive shall have no further rights against the Company hereunder, except for the right to receive: (A) the Accrued Obligations; and (B) Severance Payments, as defined below, but only for so long as Executive complies with the
requirements of Articles IV, V, VI, VII, VIII, IX and X, below. For purposes of this Agreement, “Severance Payments” means: (1) nine (9) months of Base Salary continuation; (2) a pro-rated annual incentive bonus
payment (based on the number of days worked in that fiscal year) for the fiscal year in which termination occurs based on actual performance-based bonus attainments for such fiscal year; and (3) to the extent it does not result in a tax or
penalty on the Company, reimbursement for that portion of the premiums paid by Executive to obtain COBRA continuation health coverage that equals the Company’s subsidy for health coverage for active employees with family coverage (if
applicable) grossed up so that Executive will be made whole for such premiums on an after-tax basis (“COBRA Continuation Payments”) for nine (9) months following the date employment terminates (provided that Executive has not
obtained health coverage from any other source and is not eligible to receive health coverage from any other employer, in which event Executive shall no longer be entitled to reimbursement), at the times provided in subsection (iii), below. The
treatment of Executive’s equity awards, if any, shall be governed by the terms of the applicable plans or grant agreements, except as explicitly provided to the contrary pursuant to this Agreement. 

(ii) Release Requirement. Notwithstanding the foregoing, the Company shall not pay to Executive, and Executive shall not
have any right to receive, the Severance Payments unless, on or before the sixtieth (60th) day following the date of termination of employment: (A) Executive has executed and delivered to the Company a release of all employment-related
claims against the Company, its affiliates, successor companies, and their past and current directors, officers, employees and agents, in a form provided to Executive by the Company (which shall preserve, to the extent applicable, any indemnity
rights Executive may be entitled to pursuant to Company by-laws, statute or any director and officer liability insurance maintained by the Company); and (B) the statutory revocation period for such release has expired. 

(iii) Timing of Payment of Severance Payments. Base Salary continuation shall commence on the first payroll date
following the expiration of the statutory revocation period, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date, and shall be paid over a nine (9) month period in accordance with the normal payroll
practices and schedule of the Company. The pro-rated annual incentive bonus payment shall be made at such time as other participants in the plan receive their payment, or, if later, on the sixtieth
(60th) day following the date of Executive’s termination of employment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date. The COBRA
Continuation Payments shall be paid on a monthly basis after Executive has paid 

  
 6 

 
the applicable COBRA premium payment, provided that (A) and (B) of Section 3.2(c)(ii) have been satisfied by such date, over a 9-month period. Notwithstanding anything to the
contrary contained in this Agreement, if: (A) Executive is a “specified employee” within the meaning of Section 1.409A-1(i) of the 409A Regulations; and (B) the Severance Payments do
not qualify for exemption from Section 409A under the short-term deferral exception to deferred compensation of Section 1.409A-1(b)(4) of the 409A Regulations, the separation pay plan exception to deferred compensation of
Section 1.409A-1(b)(9) of the 409A Regulations, or any other exception under the 409A Regulations, that portion of the Severance Payments not exempt from Section 409A of the Code shall be made in accordance with the terms of this
Agreement, but in no event earlier than the first to occur of: (1) the day after the six-month anniversary of Executive’s termination of employment; or (2) Executive’s death. Any payments delayed pursuant to the prior sentence
shall be made in a lump sum, on the first business day after the six-month anniversary of Executive’s termination of employment along with interest thereon payable at the short-term applicable federal rate for monthly payments, as determined
under Section 1274(d) of the Code, for the month in which Executive’s employment terminated. 
 (iv) Treatment
of Severance Payments for Tax and Benefit Purposes. The Severance Payments shall be treated as ordinary income and shall be reduced by any applicable income or employment taxes which are required to be withheld under applicable law, and all
amounts are stated before any such deduction. Furthermore, the Severance Payments shall not be included as compensation for purposes of any qualified or nonqualified retirement or welfare benefit plan, program or policy of the Company. 

(d) Parachute Payments. Notwithstanding anything contained in this Agreement to the contrary, the Company, based on the
advice of its legal or tax counsel, shall compute whether there would be any “excess parachute payments” payable to Executive, within the meaning of Section 280G of the Code, taking into account the total ‘‘parachute
payments,” within the meaning of Section 280G of the Code, payable to Executive by the Company under this Agreement and any other plan, agreement or otherwise. If there would be any excess parachute payments, the Company, based on the
advice of its legal or tax counsel, shall compute the net after-tax proceeds related to such parachute payments, taking into account the excise tax imposed by Section 4999 of the Code, as if: (i) such parachute payments were reduced, but
not below zero, such that the total parachute payments payable to Executive would not exceed three (3) times the “base amount” as defined in Section 280G of the Code, less One Dollar ($1.00); or (ii) the full amount of such
parachute payments were not reduced. If reducing the amount of such parachute payments otherwise payable would result in a greater after-tax amount to Executive, such reduced amount shall be paid to Executive and the remainder shall be forfeited. If
not reducing such parachute payments otherwise payable would result in a greater after-tax amount to Executive, then such parachute payments shall not be reduced. If such parachute payments are reduced pursuant to the foregoing, they will be reduced
in the following order: first, by reducing any cash severance payments, then by reducing any fringe or other severance benefits, and finally by reducing any payments or benefits 

  
 7 

 
otherwise payable with respect to, or measured by, the Company’s common stock (including without limitation by eliminating accelerated vesting, in each case starting with the installment or
tranche last eligible to become vested absent the occurrence of a change in control). Notwithstanding the foregoing, to the extent the Parties agree that any of the foregoing amounts are not parachute payments, such amounts shall not be reduced. To
the extent the Parties cannot agree as to whether any of the payments are in fact parachute payments, the Parties will designate, by mutual agreement, an unrelated third-party with tax expertise to make the determination. Notwithstanding any
provision of this Section 3.2(d) to the contrary, no amount shall be subject to reduction pursuant to this Section 3.2(d) to the extent the reduction would result in a violation of any applicable law. 

ARTICLE IV 

CONFIDENTIALITY 
 4.1
Confidentiality Obligations. 
 (a) During Employment. Executive will not, during Executive’s employment
with the Company, directly or indirectly use or disclose any Confidential Information or Trade Secrets except in the interest and for the benefit of the Company. 

(b) Trade Secrets Post-Employment. After the end, for any reason, of Executive’s employment with the Company,
Executive will not directly or indirectly use or disclose any Trade Secrets. 
 (c) Confidential Information
Post-Employment. For a period of twenty-four (24) months following the end, for any reason, of Executive’s employment with the Company, Executive will not directly or indirectly use or disclose any Confidential Information. 

(d) Third Party Information. Executive further agrees not to use or disclose at any time information received by the
Company from others except in accordance with the Company’s contractual or other legal obligations. 
 4.2 Definitions. 

(a) Trade Secret. The term “Trade Secret” has that meaning set forth under applicable law. 

(b) Confidential Information. The term “Confidential Information” means all non-Trade Secret
information of, about or related to the Company or provided to the Company by its customers and suppliers that is not known generally to the public or the Company’s competitors. Confidential Information includes, but is not limited to:
(i) strategic plans, budgets, forecasts, financial information, inventions, product designs and specifications, material specifications, materials sourcing information, product costs, information about products under development, research and
development information, production processes, equipment design and layout, customer lists, information about orders from and transactions with customers, sales and marketing information, strategies and plans, pricing information; and
(ii) information which is marked or otherwise designated or treated as confidential or proprietary by the Company. 

(c) Exclusions. Notwithstanding the foregoing, the terms “Confidential Information” and “Trade
Secret” do not include, and the obligations set forth in this Agreement do not apply to, any information which: (i) can be demonstrated by Executive to have been known by Executive prior to Executive’s employment by the Company;
(ii) is or becomes generally available to the public through no act or omission of Executive; (iii) is obtained by Executive in good faith from a third party who discloses such information to Executive on a non-confidential basis without
violating any obligation of confidentiality or secrecy relating to the information disclosed; or (iv) is independently developed by Executive outside the scope of Executive’s employment without use of Confidential Information or Trade
Secrets of the Company. 

  
 8 

 ARTICLE V 

NON-COMPETITION 
 5.1
Restrictions on Competition During Employment. During the term of Executive’s employment with the Company, Executive shall not directly or indirectly compete against the Company, or directly or indirectly divert or attempt to divert any
Customer’s business from the Company anywhere the Company does or is taking steps to do business. 
 5.2 Post-Employment Restricted
Services Obligation. For a period of two (2) years following the end, for whatever reason, of Executive’s employment with the Company, Executive agrees not to directly or indirectly provide Restricted Services to any Competitor in the
Territory. 
 5.3 Definitions. 

(a) Restricted Services. The term “Restricted Services” means employment duties and functions of the
type provided by Executive to the Company during the twelve (12) month period immediately prior to the end, for whatever reason, of Executive’s employment with the Company. 

(b) Competitor. The term “Competitor” means Carhartt, Inc., L.L. Bean, Inc., Cabela’s Inc.,
Land’s End, Inc., VF Corporation, and any and all of their respective affiliates and successors. In addition, the term “Competitor” shall mean any corporation, partnership, association, or other person or entity that engages in any
business which, at any time during the eighteen (18) month period immediately prior to the end, for whatever reason, of Executive’s employment with the Company, and regardless of business format (including, but not limited to, department
stores, specialty stores, discount stores, direct marketing, or electronic commerce): (i) marketed, manufactured, or sold men’s or women’s work wear of the type marketed, manufactured or sold by the Company during the eighteen
(18) month period immediately prior to the end of Executive’s employment with the Company; and (ii) had combined annual revenues in excess of $100 million. 

(c) Territory. The term “Territory” shall mean the United States of America and Canada. 

  
 9 

 ARTICLE VI 

BUSINESS IDEA RIGHTS 
 6.1
Assignment. The Company will own, and Executive hereby assigns to the Company and agrees to assign to the Company, all rights in all Business Ideas which Executive originates or develops whether alone or working with others while Executive is
employed by the Company. All Business Ideas which are or form the basis for copyrightable works are hereby assigned to the Company and/or shall be assigned to the Company or shall be considered “works for hire” as that term is defined by
United States Copyright Law. 
 6.2 Definition of Business Ideas. The term “Business Ideas” means all ideas,
designs, modifications, formulations, specifications, concepts, know-how, trade secrets, discoveries, inventions, data, software, developments and copyrightable works, whether or not patentable or registrable, which Executive originates or develops,
either alone or jointly with others while Executive is employed by the Company and which are: (i) related to any business known to Executive to be engaged in or contemplated by the Company; (ii) originated or developed during
Executive’s working hours; or (iii) originated or developed in whole or in part using materials, labor, facilities or equipment furnished by the Company. 

6.3 Disclosure. While employed by the Company, Executive will promptly disclose all Business Ideas to the Company. 

6.4 Execution of Documentation. Executive, at any time during or after the Employment Term, will promptly execute all documents which
the Company may reasonably require to perfect its patent, copyright and other rights to such Business Ideas throughout the world. 

ARTICLE VII 

NON-SOLICITATION OF EMPLOYEES 

During the term of Executive’s employment with the Company and for two (2) years thereafter, Executive shall not directly or
indirectly encourage any Company employee to terminate employment with the Company or solicit such an individual for employment outside the Company in any manner which would end or diminish that employee’s services to the Company. 

ARTICLE VIII 
 EMPLOYEE
DISCLOSURES AND ACKNOWLEDGMENTS 
 8.1 Confidential Information of Others. Executive warrants and represents to the Company that
Executive is not subject to any employment, consulting or services agreement, or any restrictive covenants or agreements of any type, which would conflict or prohibit Executive from fully carrying out Executive’s duties as described under the
terms of this Agreement. Further, Executive warrants and represents to the Company that Executive has not and will not retain or use, for the benefit of the Company, any confidential information, records, trade secrets, or other property of a former
employer. 

  
 10 

 8.2 Scope of Restrictions. Executive acknowledges that during the course of
Executive’s employment with the Company, Executive will gain knowledge of Confidential Information and Trade Secrets of the Company. Executive acknowledges that the Confidential Information and Trade Secrets of the Company are necessarily
shared with Executive on a routine basis in the course of performing Executive’s job duties and that the Company has a legitimate protectable interest in such Confidential Information and Trade Secrets, and in the goodwill and business
prospects associated therewith. Executive acknowledges that the Company does business in all states in the United States and in Canada. Accordingly, Executive acknowledges that the scope of the restrictions contained in this Agreement are
appropriate, necessary and reasonable for the protection of the business, goodwill and property rights of the Company, and that the restrictions imposed will not prevent Executive from earning a living in the event of, and after, the end, for any
reason, of Executive’s employment with the Company. 
 8.3 Prospective Employers. Executive agrees, during the term of any
restriction contained in Articles IV, V, VI, VII, VIII, IX and X of this Agreement, to disclose this Agreement to any entity which offers employment or engagement to Executive. Executive further agrees that, during the term of any restriction
contained in Articles IV, V, VI, VII, VIII, IX and X, the Company may send a copy of this Agreement to, or otherwise make the provisions hereof known to, any person or entity with which Executive seeks to establish a business relationship,
including, without limitation, potential employers, joint-venturers, or persons or entities to whom Executive seeks to provide consulting services as an independent contractor. 

8.4 Third Party Beneficiaries. All of the Company’s affiliates, successors and assigns are third party beneficiaries with respect
to Executive’s performance of Executive’s duties under this Agreement and the undertakings and covenants contained in this Agreement, and the Company and any such entity, enjoying the benefits thereof, may enforce this Agreement directly
against Executive. 
 8.5 Survival. The Covenants set forth in Articles IV, V, VI, VII, VIII, IX and X of this Agreement shall
survive the termination of this Agreement. 
 8.6 Injunctive Relief. Executive acknowledges that the services to be rendered by
Executive hereunder are of a special, unique, and extraordinary character and, in connection with such services, Executive will have access to Confidential Information and Trade Secrets that are vital to the Company’s business. Executive
consents and agrees that, in the event of the breach or a threatened breach by Executive of any of the provisions of this Agreement, the Company would sustain irreparable harm and that damages at law would not be an adequate remedy for a violation
of this Agreement, and, in addition to any other rights or remedies that the Company may have under this Agreement, common or statutory law or otherwise, the Company shall be entitled to specific performance and/or injunctive or other equitable
relief from a court of competent jurisdiction enforcing this Agreement and/or restraining Executive from committing, threatening to commit, or continuing any violation of this Agreement (in each case without posting a bond or other security),
including, but not limited to, restraining Executive from disclosing, using for any purpose, selling, transferring, or otherwise disposing of, in whole or in 

  
 11 

 
part, any Confidential Information and/or Trade Secrets. Nothing contained herein shall be construed as prohibiting the Company from pursuing any other remedies available to it for any breach or
threatened breach of any provision of this Agreement, including, but not limited to, the recovery of damages, costs, and fees, including the recovery of any prior Severance Payments made to Executive. 

8.7 Consistency With Applicable Law. Executive acknowledges and agrees that nothing in this Agreement prohibits Executive from
reporting possible violations of law to any governmental agency or entity or making other disclosures that are protected under the whistleblower provisions of federal, state or local laws or regulations. 

ARTICLE IX 
 RETURN OF
RECORDS 
 Upon the end, for any reason, of Executive’s employment with the Company, or upon request by the Company at any time,
Executive, within five (5) days after the termination of Executive’s employment or earlier upon the Company’s written request, shall return to the Company all documents, records, information, equipment (including computers, laptops,
tablet computers, cell phones and other such equipment (“Electronic Equipment”)) and materials belonging and/or relating to the Company (except Executive’s own personnel and wage and benefit materials relating solely to
Executive and Executive’s personal Electronic Equipment which is not owned by the Company), all passwords and/or access codes related to such equipment and/or materials, and all copies of all such materials. Upon the end, for any reason, of
Executive’s employment with the Company, or upon request of the Company at any time, Executive further agrees to destroy such records maintained by Executive on Executive’s personally-owned Electronic Equipment, which destruction the
Company may reasonably confirm. 
 ARTICLE X 

NONDISPARAGEMENT 

Executive agrees that Executive will not, at any time (whether during or after the Employment Term), publish or communicate to any person or
entity any Disparaging (as defined below) remarks, comments or statements concerning the Company and its respective present and former members, partners, directors, officers, shareholders, employees, agents, attorneys, successors and assigns, except
as required by law, rule or regulation. “Disparaging” remarks, comments or statements are those that impugn the character, honesty, integrity or morality or business acumen or abilities in connection with any aspect of the operation
of business of the individual or entity being disparaged. 

  
 12 

 ARTICLE XI 

MISCELLANEOUS 
 11.1
Notice. Notices and all other communications provided for in this Agreement shall be in writing and shall be delivered personally or sent by registered or certified mail, return receipt requested, postage prepaid, or sent by electronic mail
or prepaid overnight courier to the Parties at the addresses set forth below (or such other address as shall be specified by the Parties by like notice pursuant to this Section 11.1): 

 

							
	To the Company:	  	Duluth Holdings, Inc.	  	
		  	[Personal Information Omitted]	  	
			
	With a copy to:	  	Godfrey & Kahn, S.C.	  	
		  	[Personal Information Omitted]	  	
			
	To Executive:	  	Mark DeOrio	  	
		  	[Personal Information Omitted]	  	

 Such notices and communications shall be deemed given upon personal delivery or receipt at the address or email account of the
party stated above or at any other address specified by such party to the other party in writing, except that if delivery is refused or cannot be made for any reason, then such notice shall be deemed given on the third day after it is sent. 

11.2 Entire Agreement; Amendment; Waiver. This Agreement (including any documents referred to herein) sets forth the entire
understanding of the Parties hereto with respect to the subject matter contemplated hereby. Any and all previous agreements and understandings between or among the Parties regarding the subject matter hereof, whether written or oral, are superseded
by this Agreement. This Agreement shall not be amended or modified except by a written instrument duly executed by each of the Parties hereto. Any extension or waiver by any party of any provision hereto shall be valid only if set forth in an
instrument in writing signed on behalf of such party. 
 11.3 Headings. The headings of sections and paragraphs of this Agreement are
for convenience of reference only and shall not control or affect the meaning or construction of any of its provisions. 
 11.4
Attorneys’ Fees; Expenses. Except as provided in Section 2.3(c), above, each party hereto shall bear and pay all of the respective fees, expenses and disbursements of their agents, representatives, accountants and counsel incurred
in connection with and related to this Agreement. 
 11.5 Waiver of Breach. The waiver by either party of the breach of any provision
of this Agreement shall not operate or be construed as a waiver of any subsequent breach by either party. 

  
 13 

 11.6 Severability. If any court of competent jurisdiction determines that any provision of
this Agreement is invalid or unenforceable, then such invalidity or unenforceability shall have no effect on the other provisions hereof, which shall remain valid, binding and enforceable and in full force and effect, and, to the extent allowed by
law, such invalid or unenforceable provision shall be construed in a manner so as to give the maximum valid and enforceable effect to the intent of the Parties expressed therein. 

11.7 Governing Law. This Agreement shall in all respects be construed according to the laws of the State of Wisconsin, without regard
to its conflict of laws principles. 
 11.8 Future Cooperation. Executive agrees that, during Executive’s employment and
following the termination of Executive’s employment for any reason, Executive will cooperate with requests by the Company to assist in the defense or prosecution of any lawsuits or claims in which the Company, or its officers, directors or
employees may be or become involved and in connection with any internal investigation or administrative, regulatory or judicial proceeding, in each case which relates to matters occurring while Executive was employed by the Company, at such times
and at such places as shall be mutually convenient for Executive and the Company, taking into account any employment commitments which Executive then has. Executive shall be compensated by the Company at a rate comparable to that which Executive
earned while an employee of the Company or that which Executive is currently earning, whichever is greater; provided, however, that during such time as Executive is receiving Severance Payments pursuant to Section 3.2(c) of this Agreement, such
Severance Payments shall be the sole compensation provided to Executive for services reasonably requested under this Section 11.8. 

11.9 Compliance with Section 409A of the Code and the 409A Regulations. This Agreement, and any ambiguity hereunder, shall be
interpreted and administered so that any payments or benefits are either exempt from or avoid taxation under Section 409A of the Code, the 409A Regulations and any authority promulgated thereunder. Executive acknowledges that the Company has
made no representations as to the treatment of the compensation and benefits provided hereunder and the Executive has been advised to obtain Executive’s own tax advice. Any term used in this Agreement which is defined in Code Section 409A
or the 409A Regulations shall have the meaning set forth therein unless otherwise specifically defined herein. Any obligations under this Agreement that are subject to the requirements of Code Section 409A and arise in connection with
Executive’s “termination of employment”, “termination” or other similar references shall only be triggered if the termination of employment or termination qualifies as a “separation from service” within the meaning
of Section 1.409A-1(h) of the 409A Regulations. Notwithstanding any other provision of this Agreement, if at the time of the termination of Executive’s employment, Executive is a “specified employee,” as defined in
Section 409A or the 409A Regulations, and any payments upon such termination under this Agreement hereof will result in additional tax or interest to Executive under Code Section 409A, Executive will not be entitled to receive such
payments until the date which is the earlier of: (i) six (6) months after the termination of Executive’s employment; or (ii) Executive’s death. Each amount or benefit payable pursuant to this Agreement shall be deemed a
separate payment for purposes of Section 409A and the 409A Regulations. 

  
 14 

 11.10 Successors. 

(a) This Agreement is personal to Executive and shall not be assignable by Executive otherwise than by will or the laws of
descent and distribution. This Agreement shall inure to the benefit of and be enforceable by Executive’s legal representatives. 

(b) This Agreement shall be assignable by the Company without the written consent of Executive and shall inure to the benefit
of and be binding upon the Company and its respective successors and assigns. Upon assignment of this Agreement by the Company, all references to the “Company” shall be deemed to refer to the party to which this Agreement is assigned. 

11.11 Acknowledgement of Representation. Executive and the Company acknowledge that they have had the opportunity to be represented by
counsel of their own choosing and, therefore, in the event of a dispute over the meaning of this Agreement or any provisions thereof, neither party shall be entitled to any presumption of correctness in favor of the interpretation advanced by such
party or against the interpretation advanced by the other party. 
 IN WITNESS WHEREOF, the Parties hereto have caused this Agreement to be
duly executed as of the date first written above. 
  

	
	EXECUTIVE:
	
	 /s/ Mark DeOrio

	Mark DeOrio
	
	DULUTH HOLDINGS, INC.:
	
	 /s/ Stephanie Pugliese

	Stephanie Pugliese
	President & Chief Executive Officer

  
 15

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