Document:

EX-10.16

 Exhibit 10.16 

2015 EQUITY INCENTIVE PLAN 

OF 
 DULUTH HOLDINGS
INC. 
 1. PURPOSE 
 The purpose of
the Plan is to provide compensation alternatives for certain Employees, Directors and Consultants using or based on the common stock of the Company. These alternatives are intended to be used to increase the long-term financial success of the
Company, and increase the value of the Company to its shareholders, by attracting and retaining key personnel who are instrumental in the continued success of the Company, and motivating key employees by providing them with the opportunity to
participate with the shareholders in the long-term growth and financial success of the Company. 
 2. DEFINITIONS 

Unless the context otherwise requires, the following terms shall have the meanings set forth below: 

(a) “Award” shall mean an Option, Shares, Restricted Stock, Restricted Stock Units, Deferred Stock or Performance Share Units
granted under the Plan. 
 (b) “Award Agreement” shall mean an Option Agreement, Restricted Stock Agreement, Restricted
Stock Unit Agreement, Deferred Stock Agreement or Performance Share Unit Agreement, as applicable. 
 (c) “Board of
Directors” shall mean the board of directors of the Company. 
 (d) “Cause” with respect to any Participant shall
have the same meaning as in any employment agreement between the Company and such Participant, if any, and otherwise shall mean termination of a Participant’s employment with the Company or service as a Consultant upon, as applicable,
(i) any failure of the Participant to substantially perform his or her duties with the Company (other than by reason of illness) which occurs after the Company has delivered to the Participant a demand for performance which specifically
identifies the manner in which the Company believes the Participant has failed to perform his or her duties, and the Participant fails to resume performance of his or her duties on a continuous basis within fourteen (14) days after receiving
such demand, (ii) such Participant’s commission of a material violation of any law or regulation applicable to the Company or a Subsidiary or the Participant’s activities in respect of the Company or a Subsidiary, (iii) such
Participant’s commission of any material act of dishonesty or disloyalty involving the Company or a Subsidiary, (iv) in the case of an Employee, such Participant’s chronic absence from work other than by reason of a serious health
condition, (v) such Participant’s commission of a crime which substantially relates to the circumstances of his or her position with the Company or a Subsidiary or which has material adverse effect on the Company or a Subsidiary, or
(vi) the willful engaging by such Participant in conduct which is demonstrably and materially injurious to the Company or a Subsidiary. 

 (e) “Change in Control” shall mean the first to occur of the following:
(i) the sale, lease, exchange, encumbrance or other disposition (other than licenses that do not constitute an effective disposition of all or substantially all of the assets of the Company and its subsidiaries taken as a whole, and the grant
of security interests in the ordinary course of business) by the Company of all or substantially all of the Company’s assets; or (ii) the merger or consolidation of the Company with or into any other entity, other than a merger or
consolidation that would result in the Class A Common Stock of the Company outstanding immediately prior thereto continuing to represent (either by remaining outstanding or by being converted into voting securities of the surviving entity or
its sole parent entity) more than fifty percent (50%) of the total voting power represented by the voting securities of the Company or such surviving entity or its sole parent entity outstanding immediately after such merger or consolidation.

 (f) “Code” shall mean the Internal Revenue Code of 1986, as amended. 

(g) “Committee” shall mean the Compensation Committee of the Board of Directors with respect to grants to Employees or
Consultants under the Plan and the Board of Directors with respect to grants to Directors under the Plan. Notwithstanding the foregoing, for grants made to Employees who are officers under Section 16 of the Exchange Act, to the extent such
grants are intended to qualify as “performance-based compensation” under Section 162(m) of the Code, the Committee shall be constituted solely of “outside directors” as described in regulations promulgated under
Section 162(m) of the Code. 
 (h) “Company” shall mean Duluth Holdings Inc., a Wisconsin corporation. 

(i) “Consultant” shall mean an individual who is a not an Employee or a member of the Board of Directors and who is providing
service, as a consultant or other service provider, to the Company or a Subsidiary. 
 (j) “Deferred Stock” shall mean a
right to receive one or more Shares from the Company in accordance with, and subject to, Paragraph 10 of the Plan. 
 (k) “Deferred
Stock Agreement” shall mean the agreement between the Company and a Participant confirming the terms under which Deferred Stock has been granted to such Participant. 

(l) “Director” shall mean an individual who is a member of the Board of Directors. 

(m) “Disability” shall mean (i) a Participant is unable 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, or (ii) a Participant is, 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, receiving income replacement benefits for a period of not less than three months under an accident
and health plan covering employees of the Participant’s employer. 
 (n) “Employee” shall mean an individual who is an
employee of the Company or a Subsidiary. 

  
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 (o) “Exchange Act” shall mean the Securities Exchange Act of 1934, as amended.

 (p) “Fair Market Value” shall mean, as of any date, the value of the Shares determined as follows: 

(1) If the Shares are listed on any established stock exchange or national market system, “Fair Market Value”
shall be the closing sales price for such stock as quoted on such exchange or system for such date. If there are no market quotations for the Shares on such date, the determination shall be made by reference to the last date preceding such date for
which there are market quotations. 
 (2) For the avoidance of doubt,on the date that the initial public offering of the
Shares occurs, “Fair Market Value” shall be the closing sale price for such stock on the date of consummation of the initial public offering. 

(3) If the Shares are regularly quoted by a recognized securities dealer but selling prices are not reported, “Fair
Market Value” shall be the mean between the high bid and low asked prices for the Shares such date. If there are no bid or asked prices for the Shares on such date, the determination shall be made by reference to the last date preceding
such date for which there are bid and asked prices. 
 (4) In the absence of an established market for the Shares,
“Fair Market Value” shall be the fair market value of a Share as determined in good faith by the Committee in conformity with applicable law and accounting standards, with the Committee’s determination being binding on the
Company, the Participants and all other persons for all purposes. 
 (q) “Fiscal Year” means the fiscal year of the
Company. 
 (r) “Good Reason” shall mean (i) a material diminution in Participant’s authority or duties,
(ii) a material reduction in Participant’s base salary (excluding, however, any reduction made in connection with, and proportionate to, a Company-wide reduction), or (iii) a material change in Participant’s location of
employment (excluding any required relocation within a 50-mile radius of such location of employment); provided, however, that the Participant has given notice of the existence of the good reason condition within 90 days of its
occurrence, and the Company has been given at least 30 days to remedy the condition and has failed to do so. 
 (s)
“Option” shall mean an option to purchase Shares which is not intended to meet the requirements of Section 422 of the Code. 

(t) “Option Agreement” shall mean the agreement between the Company and a Participant confirming the terms under which an
Option has been granted to such Participant. 
 (u) “Participant” shall mean an Employee, Director or Consultant to whom an
Award has been granted under the Plan. 
 (v) “Performance Goals” shall mean the goals identified by the Committee to
measure one or more business or other criteria, which may include any of the following criteria 

  
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and which, where applicable (i) may be set on a pre-tax or after-tax basis, (ii) may include or exclude the impact of changes in currency exchange rates, (iii) may be applied on an
absolute or relative basis, (iv) may be valued on a growth or fixed basis, and (v) may be applied on a Company-wide, business segment, or individual basis, all as specified at the time of grant: 

(1) net income; 

(2) revenue; 

(3) earnings per share; 

(4) return on investment; 

(5) return on invested capital; 

(6) return on equity; 

(7) return on assets or net assets; 

(8) shareholder returns (either including or excluding dividends) over a specified period of time; 

(9) financial return ratios; 

(10) cash flow (including, but not limited to, operating cash flow, free cash flow, cash flow return on equity, and cash flow
return on investment); 
 (11) amount of expense; 

(12) economic profit; 

(13) gross profit; 

(14) gross profit margin percentage; 

(15) operating profit; 

(16) operating profit margin percentage; 

(17) amount of indebtedness; 

(18) debt ratios; 

(19) earnings before bonus, interest, taxes, depreciation or amortization (or any combination thereof); 

(20) Share value; 

(21) return on capital employed; 

(22) return on average capital employed; 

(23) strategic business criteria, consisting of one or more objectives based on achieving specified revenue, market
penetration, or geographic business expansion goals, or cost targets, or goals relating to acquisitions or divestitures, or any combination of the foregoing; 

(24) customer satisfaction; 

(25) productivity ratios; 

(26) new product invention or innovation; 

(27) attainment of research and development milestones; or 

(28) such other subjective or objective performance measures, including individual goals deemed appropriate by the Committee.

 The above Performance Goals may be determined with or without regard to unusual or infrequent items, including, without limitation:
changes in accounting principles or the application thereof; unusual or infrequent gains; gains or losses on the sale of assets; currency fluctuations, acquisitions, divestitures, or necessary financing activities; recapitalizations, including stock
splits and dividends; expenses for restructuring activities; and other non-operating items, as specified by the Committee upon the grant of an Award. 

  
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 (w) “Performance Share Units” shall mean a right to receive Shares from the
Company upon the attainment of specified Performance Goals in accordance with, and subject to, Paragraph 11 of the Plan. 
 (x)
“Performance Share Unit Agreement” shall mean the agreement between the Company and a Participant confirming the terms under which Performance Share Units have been granted to the Participant. 

(y) “Plan” shall mean the 2015 Equity Incentive Plan of the Company. 

(z) “Restricted Period” shall mean the period prior to which all Shares subject to, or issued in respect of, an Award have
vested. 
 (aa) “Restricted Stock” shall mean Shares granted to a Participant by the Committee which are subject to
restrictions imposed under Paragraph 9 of the Plan. 
 (bb) “Restricted Stock Agreement” shall mean the agreement between
the Company and a Participant confirming the terms under which Restricted Stock has been granted to such Participant. 
 (cc)
“Restricted Stock Units” shall mean a right to receive Shares from the Company in accordance with, and subject to, Paragraph 9 of the Plan. 

(dd) “Restricted Stock Unit Agreement” shall mean the agreement between the Company and a Participant confirming the terms
under which Restricted Stock Units have been granted to such Participant. 
 (ee) “Share” or “Shares”
shall mean the no par value Class B common stock of the Company. 
 (ff) “Subsidiary” shall mean any entity in which the
Company owns, directly or indirectly, more than 50% of the voting interests entitled to vote in the election of directors, or any comparable governing body if the entity does not have directors. 

3. AWARDS AVAILABLE UNDER THE PLAN 
 The
Committee may grant Options, Shares, Restricted Stock, Restricted Stock Units, Deferred Stock and Performance Share Units under the Plan. 
 4. SHARES
RESERVED UNDER PLAN 
 (a) The aggregate number of Shares which may be issued under the Plan pursuant to the exercise, settlement or
grant of Awards is [●]1 Shares. Shares issued under the Plan may be treasury Shares or authorized but unissued Shares, or a combination of the two, subject to adjustment as provided in
Paragraph 14 hereof. For purposes of determining the maximum 
  
  

	1 	 5% of the number of shares of Class A and Class B common stock after giving effect to the the initial public offering of the Company’s Class
B common stock. 

  
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number of Shares available for issuance under the Plan, (i) any Shares which have been issued as Restricted Stock which are forfeited to the Company shall be treated, following such
forfeiture, as Shares which have not been issued, (ii) Shares tendered, either actually or by attestation, to the Company as full or partial payment for such exercise of an Option under this Plan shall be treated as issued hereunder, and
(iii) any Shares which are used in settlement of tax withholding obligations with respect to an Award shall be treated as issued hereunder. 

(b) The number of Shares available for issuance under the Plan will be increased on the first day of each Fiscal Year beginning with the first
Fiscal Year following the Fiscal Year in which the initial public offering of the Shares occurs and continuing until the fourth Fiscal Year following the Fiscal Year in which the initial public offering of the Shares occurs, in an amount equal to
1.25% of the sum of the number of outstanding shares of Class A common stock of the Company and the number of outstanding Shares on the last day of the immediately preceding Fiscal Year. 

(c) No individual Participant shall be eligible to receive grants of Options for more than an aggregate of [●]2 Shares during any Fiscal Year (subject to adjustment as provided in Paragraph 14 hereof). 

(d) The aggregate number of shares of Restricted Stock that are subject to vesting based on Performance Goals plus the number of Restricted
Stock Units that are subject to vesting based on Performance Goals granted to any one Participant during any Fiscal Year shall be limited to [●]3 (subject to adjustment
as provided in Paragraph 14 hereof.) 
 (e) The maximum number of Performance Share Units granted to any one Employee during any Fiscal Year
shall be limited to [●]4 (subject to adjustment as provided in Paragraph 14 hereof). For purposes of this limitation, the maximum number of Performance Share Units granted shall be
determined based on the maximum number of Shares issuable under an Award of Performance Share Units, rather than the target number of Shares issuable thereunder 

5. ADMINISTRATION OF THE PLAN 
 The Plan
shall be administered by the Committee, which shall have full and exclusive power to interpret the Plan, to determine the Employees, Directors or Consultants to whom Awards are granted under the Plan, the terms and provisions of each such Award, to
grant waivers of Award restrictions, and to adopt such rules, regulations and guidelines for carrying out the Plan as it may deem necessary or proper. All determinations of the Committee under the Plan shall be in its sole discretion and are binding
on the Company, the Participants and all other persons. Except as otherwise determined by the Board of Directors, the Committee shall be so constituted as to permit grants to be exempt from Section 16(b) of the Exchange Act by virtue of Rule
16b-3 thereunder, as such rule is currently in effect or as hereafter modified or amended (“Rule 16b-3”), and to permit the Plan to comply any other statutory rule or regulatory requirements. 

 

	2 	50% of the amount of Shares reserved under Section 4(a). 

	3 	50% of the amount of Shares reserved under Section 4(a). 

	4 	 50% of the amount of Shares reserved under Section 4(a). 

  
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 6. DELEGATION OF AUTHORITY 

Except to the extent prohibited by applicable law or the applicable rules of a stock exchange, the Committee may delegate to the chief
executive officer and to other senior officers of the Company its duties under the Plan pursuant to such conditions or limitations as the Committee may establish. Any such delegation may be revoked by the Committee at any time. Consistent with the
foregoing, any delegation of authority may not extend to Awards or decisions governing persons who are directors or officers of the Company under Section 16 of the Exchange Act. 

7. ELIGIBILITY 
 Employees, Directors and
Consultants shall be eligible to receive Awards under the Plan. In determining the Employees, Directors and Consultants to whom Awards shall be granted and the number of Shares to be covered by each Award, the Committee may take into account the
nature of the services rendered by the respective Employees, Directors and Consultants, their present and potential contributions to the success of the Company, and other such factors as the Committee in its sole discretion shall deem relevant. 

8. OPTIONS 
 Options granted under this
Plan shall be subject to such terms and conditions not inconsistent with the Plan as the Committee shall determine, including the following: 

(a) Grants. Any grant of an Option shall be confirmed by the execution of an Option Agreement. 

(b) Option Exercise Price. The per share purchase price of the Shares under each Option granted pursuant to this Plan shall be
determined by the Committee but shall not be less than one hundred percent (100%) of the Fair Market Value of a Share on the date of grant of such Option. 

(c) Vesting Conditions; Exercise Period. 

(1) The Committee shall have the authority to establish the terms of any Option including the conditions under which an Option
and/or Shares that may be or are acquired upon exercise of an Option shall vest and other terms and conditions under which an Option may be exercised and Shares may be acquired upon such exercise. The Committee may set vesting conditions based
solely upon the continued employment of a Participant who is an Employee or the continued service of a Participant who is a Consultant or a Director during the applicable vesting period and/or may specify vesting conditions based upon the
achievement of specific Performance Goals. 
 (2) Except as determined by the Committee or as otherwise provided in this
Plan, upon a Participant ceasing to be an Employee, a Director, or a Consultant, as the case may be, such Participant shall forfeit any Option or portion of an Option that was granted to such Participant in such capacity and that has not vested at
the time of such cessation. 

  
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 (3) The Committee in its sole discretion may grant an Option that is fully vested
or establish a vesting schedule with respect to an Option. Except as otherwise determined by the Committee, an Option (i) shall be exercisable only to the extent the Option is vested and (ii) shall vest according to the following schedule:
(A) the Option shall vest as to one fourth of the Shares covered by the Option on the first anniversary of the date of grant of the Option, and (B) the Option shall vest as to another one fourth of the Shares covered by the Option on each
of the three (3) subsequent anniversaries of such date, provided that the Participant is still an Employee, a Director, or a Consultant, as the case may be, on each such vesting date. The Committee may permit the exercise of an Option to the
extent unvested. If so permitted, then upon the exercise of an Option or portion of an Option that has not vested, the Shares received pursuant to such exercise to the extent attributable to the unvested portion of the Option shall be Restricted
Stock subject to Paragraph 9 hereof, and having a vesting schedule the same as the vesting schedule of the Option or portion of the Option in respect of which the Shares were received. 

(4) Notwithstanding the foregoing, except as otherwise determined by the Committee, all outstanding Options held by a
Participant shall become fully vested and immediately exercisable in full, upon the first to occur of the Participant’s death or Disability while an Employee, Director or Consultant, as the case may be. 

(5) Notwithstanding the foregoing, no Option shall be exercisable after the expiration of ten (10) years from its date of
grant. Every Option which has not been exercised within ten (10) years of its date of grant shall lapse upon the expiration of such ten year period unless it shall have lapsed at an earlier date. 

(d) Exercise. Except as otherwise permitted by the Committee, an Option shall be exercisable by delivery to the Company of
(i) payment in full of the exercise price of the Shares then being acquired as provided in Paragraph 8(e) hereof, and (ii) execution of such other documentation as is determined to be necessary or appropriate by the Committee from time to
time the form of which shall be provided to the Participant at the time of execution and delivery of the Option Agreement. 
 (e) Payment
of Exercise Price. The exercise price shall be payable in whole or in part in cash (including through participation in a broker-assisted cashless exercise program), Shares held by the Participant, other property, or such other consideration
consistent with the Plan’s purpose and applicable law as may be determined by the Committee from time to time. Such price shall be paid in full at the time that an Option is exercised. If the Participant elects to pay all or a part of the
exercise price in Shares, such Participant may make such payment by delivering to the Company a number of Shares already owned by the Participant, either directly or by attestation, which are equal in value to the purchase or exercise price. All
Shares so delivered shall be valued for this purpose at their fair market value determined in the sole discretion of the Committee on the day on which such Shares are delivered. The Committee 

  
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may, in its discretion, permit a Participant to exercise an Option on a “net exercise” basis. In such case, the Company will deliver that number of Shares to the Participant which
equals the number of Shares for which the Option was exercised, reduced by the number of whole Shares (which the Company shall retain) with a value on the date of exercise (based on the Fair Market Value) equal to the exercise price and the required
tax withholding at the time of exercise. To the extent the combined value of the whole Shares is not sufficient to equal the exercise price and required tax withholding, the Participant must pay such difference in cash to the Company before delivery
of the Shares will be made to the Participant. 
 (f) Cessation of Status. Except as determined otherwise by the Committee: 

(1) Any Participant who ceases to be an Employee, Director or Consultant due to Disability shall have one (1) year from
the date of such cessation to exercise any Option granted hereunder as to all or part of the Shares subject to such Option; provided, however, that no Option shall be exercisable subsequent to ten (10) years from its date of
grant. 
 (2) In the event of the death of a Participant while an Employee, a Director, or a Consultant, as the case may be,
any Option, as to all or any part of the Shares subject to such Option, granted to such Participant shall be exercisable: 

(A) for one (1) year after the Participant’s death, but in no event subsequent to ten (10) years from its date
of grant; and 
 (B) only (i) by the deceased Participant’s designated beneficiary (such designation to be made in
writing at such time and in such manner as the Committee shall approve or prescribe), or, (ii) if the deceased Participant dies without a surviving designated beneficiary, by the personal representative, administrator, or other representative
of the estate of the deceased Participant, or by the person or persons to whom the deceased Participant’s rights under the Option shall pass by will or the laws of descent and distribution. 

A Participant who holds (including following cessation of employment or service) an Option who has designated a beneficiary for purposes of
Subparagraph 8(f)(2)(B)(i) hereof may change such designation at any time, by written notice given to the Secretary of the Company, subject to such conditions and requirements as the Committee may prescribe in accordance with applicable law. 

(3) If a Participant ceases to be an Employee, Director or Consultant for a reason other than those specified above, such
Employee or Consultant (with respect to an Option granted to him or her in the capacity of an Employee or Consultant) or Director (with respect to an Option granted to him or her in the capacity of a Director) shall have ninety (90) days from
the date of such cessation to exercise any such Option with respect to such of the Shares subject thereto as to which such Participant then has a present right to exercise; provided, however, that no Option shall be exercisable
subsequent to ten (10) years from its date of grant. Notwithstanding the foregoing, if a person ceases to be an Employee or a Consultant because of a termination of employment or service for Cause, to the extent an Option is not effectively
exercised prior to such cessation, it shall lapse immediately upon such cessation. 

  
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 (g) Extension of Periods. The Committee in its sole discretion may increase the periods
permitted for exercise of an Option if a Participant ceases to be an Employee, Director or Consultant as provided in Subparagraphs 8(f)(1), (2) and (3) hereof if allowable under applicable law; provided, however, in no event
shall an Option be exercisable subsequent to ten (10) years after its date of grant. 
 (h) Transferability. Except as otherwise
provided in the remainder of this Paragraph 8(h) or determined by the Committee, an Option shall not be transferable or subjected to execution, attachment or similar process, and during the lifetime of the Participant shall be exercisable only by
the Participant. A Participant shall have the right to transfer an Option granted to such Participant upon such Participant’s death, either to the deceased Participant’s designated beneficiary (such designation to be made in writing at
such time and in such manner as the Committee shall approve or prescribe), or, if the deceased Participant dies without a surviving designated beneficiary, by the terms of such Participant’s will or under the laws of descent and distribution,
subject to any limitations set forth in this Plan or otherwise determined by the Committee, and all such transferees shall be subject to all terms and conditions of this Plan to the same extent as would be the Participant. 

(i) Nature of Options. No Participant shall have any interest in any fund or in any specific asset or assets of the Company by reason
of any Options granted hereunder, or any right to exercise any of the rights or privileges of a shareholder with respect to any Options until Shares are issued in connection with any exercise. 

9. RESTRICTED STOCK / RESTRICTED STOCK UNITS 

Restricted Stock or Restricted Stock Units granted under this Plan shall be subject to such terms and conditions not inconsistent with the Plan
as the Committee shall determine, including the following: 
 (a) Grants. The terms of any grant of Restricted Stock or Restricted
Stock Units shall be confirmed by the execution of a Restricted Stock Agreement or Restricted Stock Unit Agreement. 
 (b) Restrictions
on Restricted Stock. Restricted Stock may not be sold, assigned, conveyed, donated, pledged, transferred or otherwise disposed of or encumbered for the Restricted Period, subject to the provisions of this Paragraph 9. In the event that a
Participant shall sell, assign, convey, donate, pledge, transfer or otherwise dispose of or encumber the Restricted Stock, such Restricted Stock shall be forfeited to the Company. 

(c) Vesting Conditions. The Committee shall determine the conditions under which Restricted Stock or Restricted Stock Units shall vest.
The Committee may set vesting conditions based solely upon the continued employment of a Participant who is an Employee or the continued service of a Participant who is a Director or Consultant during the applicable vesting period and/or may specify
vesting conditions based upon the achievement of specific Performance Goals. For purposes of qualifying Restricted Stock or Restricted Stock Units as “performance-based compensation” 

  
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under Section 162(m) of the Code, the Committee may set performance conditions based upon the achievement of Performance Goals. In such event, the Performance Goals shall be set by the
Committee on or before the latest date permissible to enable the Restricted Stock or Restricted Stock Units to qualify as “performance-based compensation” under Section 162(m) of the Code and the Committee shall follow any procedures
determined by it from time to time to be necessary or appropriate to ensure qualification of the Restricted Stock or Restricted Stock Units under Section 162(m) of the Code, including, without limitation, written certification by the Committee
that the Performance Goals and other applicable conditions have been satisfied before the Restricted Period shall end or the Restricted Stock Units are paid. 

(d) Cessation of Status. Except as determined otherwise by the Committee: 

(1) If a Participant ceases to be an Employee, a Director or a Consultant for any reason, then except as provided in
Subparagraph 9(d)(2) hereof, such Employee or Consultant (with respect to Restricted Stock or Restricted Stock Units granted to him or her in the capacity of an Employee or a Consultant), or such Director (with respect to Restricted Stock or
Restricted Stock Units granted to him or her in the capacity of a Director) shall forfeit all Restricted Stock and all unvested Restricted Stock Units held by such Participant. 

(2) Upon the death or Disability of an Employee, Director or Consultant, while employed or otherwise providing services to the
Company, all restrictions applicable to any Restricted Stock then held by such a Participant shall immediately lapse and all unvested Restricted Stock Units held by such a Participant shall immediately vest. 

(e) Retention of Certificates. The Company will retain custody of the stock certificates representing Restricted Stock during the
Restricted Period, as well as a stock power signed by the Participant to be used in the event the Restricted Stock is forfeited to the Company. 

(f) Transferability of Restricted Stock Units. Except as provided below, Restricted Stock Units may not be sold, assigned, conveyed,
donated, pledged, transferred or otherwise disposed of or encumbered or subjected to execution, attachment, or similar process; provided, however, Shares distributed in respect of such Restricted Stock Units may be transferred in
accordance with applicable securities laws. Any transfer, attempted transfer, or purported transfer of Restricted Stock Units by a Participant shall be null and void. A Participant shall have the right to transfer Restricted Stock Units upon such
Participant’s death, either to the deceased Participant’s designated beneficiary (such designation to be made in writing at such time and in such manner as the Committee shall prescribe or approve), or, if the deceased Participant dies
without a surviving designated beneficiary, by the terms of such Participant’s will or under the laws of descent and distribution, subject to any limitations set forth in the Plan or otherwise determined by the Committee, and all such
transferees shall be subject to all terms and conditions of the Plan to the same extent as would the Participant. 
 (g) No Rights as
Shareholders for Participants Holding Restricted Stock Units. No Participant shall have any interest in any fund or in any specific asset or assets of the Company by reason of any Restricted Stock Units granted hereunder, nor any right to
exercise any of the rights or privileges of a shareholder with respect to any Restricted Stock Units or any Shares distributable with respect to any Restricted Stock Units until such Shares are so distributed. 

  
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 (h) Distribution of Shares with Respect to Restricted Stock Units. Each Participant who
holds Restricted Stock Units shall be entitled to receive from the Company one Share for each Restricted Stock Unit, as adjusted from time to time in the manner set forth in Paragraph 14, below. However, the Company, as determined in the sole
discretion of the Committee at the time of grant only, shall be entitled to settle its obligation to deliver Shares by instead making a payment of cash substantially equal to the fair market value of the Shares it would otherwise be obligated to
deliver, or by the issuance of a combination of Shares and cash, in the proportions determined by the Committee, substantially equal to the fair market value of the Shares the Company would otherwise be obligated to deliver. The fair market value of
a Share for this purpose will mean the Fair Market Value on the business day immediately preceding the date of the cash payment. Except as otherwise determined by the Committee at the time of the grant, Restricted Stock Units shall vest and Shares
shall be distributed to the Participant in respect thereof as of the vesting date; provided, however, if any grant of Restricted Stock Units to a Participant who is subject to U.S. federal income tax is nonqualified deferred
compensation for purposes of Section 409A of the Code, cash or Shares shall only be distributed in a manner such that Section 409A of the Code will not cause the Participant to become subject to penalties and/or interest thereunder; and
provided, further, that no cash or Shares shall be distributed in respect of Restricted Stock Units prior to the date on which such Restricted Stock Units vest, except in cases where FICA tax withholding would be due prior to vesting.

 (i) Dividends and Distributions with Respect to Restricted Stock Units. Except as otherwise provided by the Committee, a
Participant who holds Restricted Stock Units shall not be entitled to receive dividends, distributions, or dividend equivalents when such payments or distributions are made with respect to the Shares distributable with respect to such Restricted
Stock Units. For record dates occurring after such Shares are distributed, the Participant shall be entitled to receive dividends or distributions if any are declared on the Shares. 

(j) Section 83(b) Election. The Committee may provide in a Restricted Stock Agreement that an Award of Restricted Stock is
conditioned upon the Participant making or refraining from making an election with respect to the Award under Section 83(b) of the Code. If a Participant makes an election pursuant to Section 83(b) of the Code concerning an Award of
Restricted Stock, the Participant shall be required to file promptly a copy of such election with the Company. 
 10. DEFERRED STOCK 

Deferred Stock granted under this Plan shall be subject to such terms and conditions not inconsistent with the Plan as the Committee shall
determine, including the following: 
 (a) Grants. The terms of any grant of Deferred Stock shall be confirmed by the execution of a
Deferred Stock Agreement. 
 (b) Distributions of Shares. Each Participant who holds Deferred Stock shall be entitled to receive from
the Company one Share for each share of Deferred Stock, as adjusted 

  
 12 

 
from time to time in the manner set forth in Paragraph 14 hereof. However, the Company, as determined in the sole discretion of the Committee at the time of grant only, shall be entitled to
settle its obligation to deliver Shares by instead making a payment of cash substantially equal to the fair market value of the Shares it would otherwise be obligated to deliver, or by the issuance of a combination of Shares and cash, in the
proportions determined by the Committee, substantially equal to the fair market value of the Shares the Company would otherwise be obligated to deliver. The fair market value of a Share for this purpose will mean the Fair Market Value on the
business day immediately preceding the date of the cash payment. Deferred Stock shall vest and Shares shall be distributed to the Participant in respect thereof at such time or times as determined in the Deferred Stock Agreement; provided,
however, that, with respect to Deferred Stock that is treated as nonqualified deferred compensation under Section 409A of the Code, Shares shall only be distributed in accordance with the rules of Section 409A and any guidance
issued thereunder (including any delay in distribution required if a Participant is a “specified employee” under Section 409A of the Code); and provided, further, that no Shares shall be distributed in respect of Deferred Stock prior
to the date on which such Deferred Stock vests. 
 (c) Cessation of Status. Except as otherwise determined by the Committee: 

(1) If a Participant ceases to be an Employee, a Director or a Consultant for any reason, then except as provided in
Subparagraph 10(c)(2) hereof, such Employee or Consultant (with respect to Deferred Stock granted to him or her in the capacity of an Employee or a Consultant) or such Director (with respect to Deferred Stock granted to him or her in the capacity of
a Director) shall forfeit all Deferred Stock held by such Participant on the date of termination that has not vested. 
 (2)
Upon the death or Disability of an Employee, Director or Consultant, all Deferred Stock then held by such Participant shall immediately vest. 

(d) Transferability. Deferred Stock may not be sold, assigned, conveyed, donated, pledged, transferred or otherwise disposed of or
encumbered or subjected to execution, attachment, or similar process; provided, however, Shares distributed in respect of such Deferred Stock may be transferred in accordance with applicable securities laws. A Participant shall have
the right to transfer Deferred Stock upon such Participant’s death, either to the deceased Participant’s designated beneficiary (such designation to be made in writing at such time and in such manner as the Committee shall prescribe or
approve), or, if the deceased Participant dies without a surviving designated beneficiary, by the terms of such Participant’s will or under the laws of descent and distribution, subject to any limitations set forth in the Plan or otherwise
determined by the Committee, and all such distributees shall be subject to all terms and conditions of the Plan to the same extent as would the Participant. 

(e) No Rights as a Shareholder. No Participant shall have any interest in any fund or in any specific asset or assets of the Company by
reason of any Deferred Stock granted hereunder, or any right to exercise any of the rights or privileges of a shareholder with respect to any Deferred Stock until Shares are distributed to the Participant. 

  
 13 

 (f) Dividends and Distributions. Except as otherwise provided by the Committee, a
Participant who holds Deferred Stock shall not be entitled to receive dividends, distributions, or dividend equivalents when such payments or distributions are made with respect to the Shares distributable with respect to the Deferred Stock. For
record dates occurring after such Shares are distributed, the Participant shall be entitled to receive dividends or distributions if any are declared on the Shares. 

(g) Accelerated Distribution. The Committee may not, at any time after Deferred Stock held by a Participant has vested, accelerate the
time that Shares or cash are or is distributed with respect to such Deferred Stock, except where such acceleration would not cause the Participant to become subject to penalties and/or interest under Section 409A of the Code. 

11. PERFORMANCE SHARE UNITS 
 Performance
Share Units granted under this Plan shall be subject to such terms and conditions not inconsistent with the Plan as the Committee shall determine, including the following: 

(a) Grants. The terms of any grant of Performance Share Units shall be confirmed by the execution of a Performance Share Unit Agreement.
The terms of any Performance Share Unit Agreement shall specify the target number of Performance Share Units established for the Participant, the applicable Performance Goals, the performance period, and any vesting period applicable to the Award.

 (b) Performance Goals. The Committee shall set performance conditions based upon the achievement of specific Performance Goals.
The Committee may also set vesting conditions based on the continued employment of a Participant who is an Employee or based on the continued service of a Participant who is a Director or Consultant, which may or may not run concurrently with the
performance period. For purposes of qualifying Performance Share Units as “performance-based compensation” under Section 162(m) of the Code, the Committee may set performance conditions based upon the achievement of Performance Goals.
In such event, the Performance Goals shall be set by the Committee on or before the latest date permissible to enable the Performance Share Units to qualify as “performance-based compensation” under Section 162(m) of the Code and the
Committee shall follow any procedures determined by it from time to time to be necessary or appropriate to ensure qualification of the Performance Share Units under Section 162(m) of the Code, including, without limitation, written
certification by the Committee that the Performance Goals and other applicable conditions have been satisfied before any payment is made in respect of an Award of Performance Share Units. 

(c) Award Calculation and Payment. The actual number of Performance Share Units earned shall be determined at the end of the
performance period, based on achievement of the applicable Performance Goals. Except as otherwise determined by the Committee at the time of grant, Awards will be paid in Shares equal to the number of Performance Share Units that have been earned at
the end of the performance period as of the later of: (i) the date the Committee has approved and certified the number of Performance Share Units that have been earned, or (ii) where applicable, the date any vesting period thereafter has
been satisfied. However, the Company, as determined in the sole discretion of the Committee at the time of grant, shall be 

  
 14 

 
entitled to settle its obligation to deliver Shares by instead making a payment of cash substantially equal to the fair market value of the Shares it would otherwise be obligated to deliver, or
by the issuance of a combination of Shares and cash, in the proportions determined by the Committee, substantially equal to the fair market value of the Shares the Company would otherwise be obligated to deliver. The fair market value of a Share for
this purpose will mean the Fair Market Value of a Share on the business day immediately preceding the date of the cash payment. Notwithstanding the foregoing, if any grant of Performance Share Units to a Participant who is subject to U.S. federal
income tax is nonqualified deferred compensation for purposes of Section 409A of the Code, Shares or cash shall only be distributed in a manner such that Section 409A of the Code will not cause the Participant to become subject to
penalties and/or interest thereunder. 
 (d) Cessation of Status. Except as otherwise determined by the Committee: 

(1) If a Participant ceases to be an Employee, a Director or a Consultant for any reason, then except as provided in
Subparagraph 11(d)(2) hereof the Participant shall forfeit all Performance Share Units that have not yet been earned and/or vested as of the date of termination. 

(2) If a Participant ceases to be an Employee, Director or Consultant due to death or Disability, all Performance Share Units
then held by the Participant that have not yet been earned and/or vested shall immediately become earned and vested to the same extent they would have otherwise been earned if 100% of the target performance condition had been achieved at the end of
the performance period. 
 (e) Transferability. Performance Share Units may not be sold, assigned, conveyed, donated, pledged,
transferred or otherwise disposed of or encumbered or subjected to execution, attachment, or similar process; provided, however, that Shares distributed in respect of such Performance Share Units may be transferred in accordance with
applicable securities laws. Any transfer, attempted transfer, or purported transfer of Performance Share Units by a Participant shall be null and void. A Participant shall have the right to transfer Performance Share Units upon such
Participant’s death, either to the deceased Participant’s designated beneficiary (such designation to be made in writing at such time and in such manner as the Committee shall prescribe or approve), or, if the deceased Participant dies
without a surviving designated beneficiary, by the terms of such Participant’s will or under the laws of descent and distribution, subject to any limitations set forth in the Plan or otherwise determined by the Committee, and all such
distributees shall be subject to all terms and conditions of the Plan to the same extent as would the Participant. 
 (f) Rights as a
Shareholder. A Participant receiving an Award of Performance Share Units shall have the rights of a shareholder only as to Shares issued under the Plan upon the attainment of specified Performance Goals and not with respect to Shares subject to
the Award but not issued to the Participant. A Participant shall be entitled to receive Shares only upon attainment of specified Performance Goals within the period specified in the Performance Share Unit Agreement, as certified by the Committee.

  
 15 

 12. FOREIGN AWARD RECIPIENTS 

Notwithstanding any provision of the Plan to the contrary, in order to comply with the laws in other countries in which the Company and its
Subsidiaries operate or have Employees, the Committee shall have the power and authority in its sole discretion to: (i) determine which Subsidiaries shall be covered by the Plan; (ii) determine which individuals outside the United States
are eligible to participate in the Plan; (iii) modify the terms and conditions of any Award granted to individuals outside the United States to comply with applicable foreign laws; (iv) establish subplans and modify exercise procedures and
other terms and procedures, to the extent the Committee determines such actions to be necessary or advisable (and such subplans and/or modifications shall be attached to this Plan as appendices); provided, however, that no such
subplans and/or modifications shall increase the share limitations contained in Paragraph 4 hereof; and (v) take any action, before or after an Award is made, that the Committee determines to be necessary or advisable to obtain approval or
comply with any local governmental regulatory exemptions or approvals. 
  
 13. LAWS
AND REGULATIONS 
 Each Award Agreement shall contain such representations, warranties and other terms and conditions as shall be
necessary in the opinion of counsel to the Company to comply with all applicable federal and state securities laws. The Company shall have the right to delay the issue or delivery of any Shares under the Plan until (i) the completion of such
registration or qualification of such Shares under any federal or state law, ruling or regulation as the Company shall determine to be necessary or advisable, and (ii) receipt from the Participant of such documents and information as the
Committee may deem necessary or appropriate in connection with such registration or qualification. 
 14. ADJUSTMENT PROVISIONS 

(a) Adjustments. In the event of any stock dividend, stock split, reverse stock split, recapitalization, merger, consolidation,
combination or exchange of shares, or the like, as a result of which shares of any class shall be issued in respect of the outstanding Shares, or the Shares shall be changed into the same or a different number of the same or another class of stock,
or into securities of another person, any distribution of cash or other property to the shareholders (other than a regular cash dividend), the total number of Shares authorized to be offered in accordance with Paragraph 4 hereof and any other
limitations contained in Paragraph 4 hereof, the number of Shares subject to each outstanding Option, the number of Shares of Restricted Stock or Restricted Stock Units then held by each Participant, the number of Shares to which each then
outstanding Award of Deferred Stock or Performance Share Units relates, and the exercise price applicable to each outstanding Option shall be adjusted in such equitable and proportionate manner as determined by the Committee. No fractional Share
shall be issued under the Plan resulting from any such adjustment but the Committee in its sole discretion may make a cash payment in lieu of a fractional Share. 

(b) Binding Effect. Any adjustment, waiver, conversion or other action taken by the Committee under this Paragraph 14 shall be
conclusive and binding on all Participants and the Company and their respective successors and assigns. 

  
 16 

 15. TAXES 

The Company shall be entitled to pay and withhold from any amounts payable by the Company to a Participant the amount of any tax which it
believes is required to be withheld under applicable law in connection with any Award, and the Company may defer making delivery of Shares until arrangements satisfactory to it have been made with respect to any such withholding obligations. If a
Participant is permitted by the Committee to do so, the Participant may, at his or her election, satisfy his or her obligation for payment of required tax withholding by having the Company retain a number of Shares having an aggregate Fair Market
Value on the date the Shares are withheld equal to the amount of the required tax withholding. If the Company will not accept Shares for payment of tax withholding, the Participant must transfer cash to the Company equal to the withholding
obligation. Any tax withheld hereunder shall not exceed the minimum required by law. 
 16. EFFECTIVENESS OF THE PLAN 

The Plan, as approved by the Board of Directors and the shareholders of the Company, shall become effective as of the date of such shareholder
approval, and any amendment and/or restatement of the Plan shall become effective as of the date of approval by the Board of Directors, except that, if any amendment or restatement is subject to shareholder approval, the date of shareholder approval
instead shall be the effective date. 
 17. EFFECT OF CORPORATE TRANSACTIONS 

(a) Merger, Consolidation or Reorganization. In the event of a merger, consolidation or reorganization with another corporation in which
the Company is not the surviving corporation or a merger, consolidation or reorganization involving the Company in which the Common Stock ceases to be publicly traded, the Committee shall, subject to the approval of the Board, or the board of
directors of any corporation assuming the obligations of the Company hereunder, take action regarding each outstanding and unexercised Award pursuant to either clause (1) or (2) below: 

(1) Appropriate provision may be made for the protection of such Award by the substitution on an equitable basis of appropriate
shares of the surviving or related corporation, provided that, for Options, the excess of the aggregate Fair Market Value of the Shares subject to such Award immediately before such substitution over the exercise price thereof, if any, is not more
than the excess of the aggregate Fair Market Value of the substituted shares made subject to such Award immediately after such substitution over the exercise price thereof, if any; or 

(2) The Committee may cancel such Award. In the event any Option is canceled, the Company, or the corporation assuming the
obligations of the Company hereunder, shall pay the Participant an amount of cash (less normal withholding taxes) equal to the excess of (i) the value, as determined by the Committee, of the property (including cash) received by the holder of a
Share as a result of such event over (ii) the exercise price of such Option, multiplied by the number of shares subject to such Award (including any unvested portion). In the event any other Award is canceled, the

  
 17 

 
Company, or the corporation assuming the obligations of the Company hereunder, shall pay the Participant an amount of cash or stock, as determined by the Committee, based upon the value, as
determined by the Committee, of the property (including cash) received by the holder of a Share as a result of such event (including payment for any unvested portion). No payment shall be made to a Participant for any Option if the exercise price
for such Option exceeds the value, as determined by the Committee, of the property (including cash) received by the holder of a share of Company Stock as a result of such event. Unless the particular Award Agreement provides otherwise, determination
of any payment under this subparagraph (a)(2) for an Award that is subject to a Performance Goal shall be based upon achievement at the target level of performance. 

(b) Effect of Change in Control upon Certain Awards. Except as otherwise determined by the Committee (in an Award Agreement or
otherwise) or except where a Participant’s entitlement to an Award is subject to a Performance Goal, upon a Participant’s involuntary termination of employment without Cause or a voluntary termination of the Participant’s employment
for Good Reason within twelve (12) months following a Change in Control, all Awards will become fully vested, and for Options, immediately exercisable. In the case of an Award under which a Participant’s entitlement to the Award is subject
to the achievement of a Performance Goal, except as otherwise determined by the Committee (in the Award Agreement or otherwise), upon the occurrence of a Change in Control, the Participant shall be deemed to have satisfied the Performance Goal(s) at
the target level of performance and such Award shall continue to vest based upon the time-based service vesting criteria, if any, to which the Award is subject. For Awards described in the preceding sentence that are assumed or maintained by the
acquiring or surviving company following a Change in Control, except as otherwise determined by the Committee (in an Award Agreement or otherwise), upon a Participant’s involuntary termination of employment without Cause or a voluntary
termination of the Participant’s employment for Good Reason within twelve (12) months following a Change in Control, the time-based service vesting criteria shall be deemed satisfied at the time of such termination. 

18. TERMINATION AND AMENDMENT 
 Unless the
Plan shall theretofore have been terminated as hereinafter provided, no Award shall be granted after the tenth (10th) anniversary of the date this Plan is approved by the shareholders of the
Company. The Board of Directors may terminate the Plan or make such modifications or amendments thereof as it shall deem advisable, including, but not limited to, such modifications or amendments as it shall deem advisable in order to conform to any
law or regulation applicable thereto; provided, however, that the Board of Directors may not, without further approval of the holders of a majority of the Shares voted at any meeting of shareholders at which a quorum is present and
voting, adopt any amendment to the Plan for which shareholder approval is required under tax, securities or any other applicable law. Except as described below, no termination, modification or amendment of the Plan may, without the consent of the
Participant, adversely affect the rights of such Participant under an outstanding Award then held by the Participant. 
 Notwithstanding the
above to the contrary, the Board of Directors may amend the Plan at any time, without the consent of any Participant, in order to cause the Plan to meet the 

  
 18 

 
requirements of Section 409A of the Code and any guidance promulgated thereunder in order to avoid causing any Participant to become subject to interest and/or penalties that would otherwise
by imposed under Section 409A of the Code. In the event this Plan is terminated, any amounts allocated to a Participant hereunder that are subject to Section 409A of the Code shall be distributed to the Participant only in a manner
permitted under Section 409A of the Code and any guidance promulgated thereunder. 
 Except as otherwise provided in this Plan, the
Committee may amend an outstanding Award or any Award Agreement; provided, however, that the Participant’s consent to such action shall be required unless the Committee determines that the action, taking into account any related
action, (i) would not materially and adversely affect the Participant or (ii) where applicable, is required in order for the Participant to avoid becoming subject to penalties and/or interest under Section 409A of the Code. The
Committee may also modify or amend the terms of any Award granted under the Plan for the purpose of complying with, or taking advantage of, income or other tax or legal requirements or practices of foreign countries which are applicable to
Employees. However, notwithstanding any other provision of the Plan, the Committee may not adjust or amend the exercise price of any outstanding Option, whether through amendment, cancellation and replacement grants, or any other means, except in
accordance with Paragraph 14 of the Plan. 
 19. OTHER BENEFIT AND COMPENSATION PROGRAMS 

Payments and other benefits received by an Employee under an Award granted pursuant to the Plan shall not be deemed a part of such
Employee’s regular, recurring compensation for purposes of the termination, indemnity or severance pay law of any country and shall not be included in, or have any effect on, the determination of benefits under any other employee benefit plan,
contract or similar arrangement provided by the Company or any Subsidiary unless expressly so provided by such other plan, contract or arrangement, unless required by law, or unless the Committee expressly determines otherwise. 

20. CLAWBACK POLICY 
 All Awards granted
under the Plan are subject to forfeiture, recovery by the Company or other action pursuant to any clawback or recoupment policy which the Company may adopt from time to time, including without limitation any such policy required to be adopted under
the Dodd-Frank Wall Street Reform and Consumer Protection Act and implementing rules and regulations thereunder, or other applicable law. No forfeiture or recovery of Awards granted under the Plan or any other action taken under any clawback or
recoupment policy will be an event giving rise to a right to resign for “good reason” or “constructive termination” (or similar term) under any agreement between a Participant and the Company. 

21. NO RIGHT TO EMPLOYMENT OR SERVICE. 

The Plan shall not confer upon any person any right to continue employment or service with the Company or a Subsidiary, nor shall it interfere
in any way with the right of the Company or such Subsidiary to terminate any person’s employment or service at any time. 

  
 19 

 22. SEVERABILITY 

In the event any provision of this Plan shall be held illegal or invalid for any reason, the illegality or invalidity shall not affect the
remaining parts of the Plan, and this Plan shall be construed and enforced as if the illegal or invalid provision had not been included. 
 23. GOVERNING
LAW 
 This Plan and all Awards and actions taken thereunder shall be governed by, and construed in accordance with, the laws of the
State of Wisconsin, applied without regard to the laws of any other jurisdiction that otherwise would govern under conflict of law principles. 

  
 20EX-10.23

 Exhibit 10.23 

S CORPORATION TERMINATION, TAX ALLOCATION AND 

INDEMNIFICATION AGREEMENT 

This S Corporation Termination, Tax Allocation and Indemnification Agreement, dated as of
            , 2015 (the “Agreement”), is made by and among Duluth Holdings Inc., a Wisconsin corporation (the “Company”), and the persons identified on the
signature pages hereto who constitute all of the shareholders of the Company on the date hereof (each individually, a “Shareholder,” and collectively, the “Shareholders”). 

RECITALS: 
 A. The Company
is an S Corporation within the meaning of Section 1361 of the Internal Revenue Code of 1986, as amended (the “Code”). 

B. The Company intends to enter into an underwriting agreement to sell shares of its Class B common stock to the public in an initial public
offering registered under the Securities Act of 1933, as amended, as described in the Registration Statement on Form S-1 initially filed by the Company with the Securities and Exchange Commission on October 6, 2015 (the “Public
Offering”). 
 C. The Shareholders are currently the only shareholders of the Company, and will continue to be so until the Public
Offering. 
 D. In connection with the Public Offering, and in order to induce the investment by the public in the Company, the Company and
the Shareholders desire to provide for the termination of the Company’s status as an S Corporation and a tax allocation and indemnification agreement in connection with tax periods prior to and following the Termination Date (as defined below),
as well as the other agreements set forth herein. 
 AGREEMENT: 

NOW, THEREFORE, for mutual consideration, the receipt and sufficiency of which are hereby acknowledged, the Company and the Shareholders do
hereby covenant and agree as follows: 
 ARTICLE 1 

DEFINITIONS 
 The following
terms, as used herein, have the following meanings: 
 “Accumulated Adjustments Account” or “AAA” shall
have the meaning assigned to that term by Section 1368(e)(1) of the Code. 
 “Agreement” shall have the meaning set
forth in the Introductory paragraph. 
 “Code” shall have the meaning set forth in Recital A. 

“Company” shall have the meaning set forth in the Introductory paragraph. 

  
 1 

 “C Short Year” shall have the meaning set forth in Section 1362(e)(1)(B) of
the Code. 
 “Final AAA Determination” shall have the meaning set forth in Section 2.3. 

“Final Determination” shall mean the earliest to occur of (i) the date on which a decision, judgment, decree or other
order has been issued by any court of competent jurisdiction or government agency with regard to the tax consequences at issue, which decision, judgment, decree or other order has become final (i.e., all allowable appeals requested by the parties to
the action have been exhausted), or (ii) the date on which the Internal Revenue Service or state taxing authority has entered into a binding agreement with the Company and/or the Shareholders, as applicable, with respect to the tax matter at
issue or has reached a final administrative or judicial determination with respect to the tax matter at issue which, whether by law or agreement, is not subject to appeal. 

“Highest Rate” shall mean the highest marginal U.S. federal, state and local income tax rate applicable to individuals or C
corporations, as applicable, for the taxable year to which such taxable income relates, taking into account the different tax rates applicable to ordinary income and capital gains, if any. 

“Post-Termination Distribution” shall mean a cash distribution during the Post-Termination Transition Period as set forth in
Section 1371(e) of the Code to the extent it does not exceed the AAA. 
 “Post-Termination Transition Period” shall
have the meaning set forth in Section 1377(b)(1) of the Code. 
 “Public Offering” shall have the meaning set forth in
Recital B. 
 “Regulations” means the Treasury Regulations promulgated under the Code. 

“S Corporation” shall have the meaning set forth in Section 1361 of the Code. 

“S Corporation Taxable Income” shall mean, for periods beginning on or after the date the Company became an S Corporation and
ending with the close of the last day of the S Short Year, the sum of (i) the Company’s items of separately stated income and gain (within the meaning of Section 1366(a)(1)(A) of the Code) reduced, to the extent applicable, by the
Company’s separately stated items of deduction and loss (within the meaning of Section 1366(a)(1)(A) of the Code) and (ii) the Company’s non-separately computed net income (within the meaning of Section 1366(a)(l)(B) of the
Code). 
 “Shareholders” shall have the meaning set forth in the Introductory paragraph. 

“S Short Year” shall have the meaning set forth in Section 1362(e)(1)(A) of the Code. 

“S Termination Year” shall have the meaning set forth in Section 1362(e)(4) of the Code. 

“Tax Liability” shall have the meaning set forth in Section 3.1. 

“Tax Proceeding” shall mean an amended return, claim for refund, audit, judicial decision or otherwise. 

“Termination Date” shall have the meaning set forth in Section 2.1. 

  
 2 

 ARTICLE 2 

TERMINATION OF S CORPORATION STATUS; DISTRIBUTIONS TO 

SHAREHOLDERS 
 2.1.
Termination of S Corporation Status. Pursuant to Section 1362(d)(2) of the Code, the Company’s status as an S Corporation shall terminate on the day on which the Company issues shares of the Company’s common stock in the
Public Offering to one or more shareholders which causes the Company to no longer qualify as a “small business corporation” as defined under Section 1361(b) of the Code (the “Termination Date”), provided, on such
Termination Date, the Company and certain of its Shareholders shall also file an election to revoke its status as an S Corporation pursuant to Section 1362(d)(1) of the Code in accordance with and in the manner provided by Regulation
§ 1.1362-6(a)(3). 
 2.2. Distribution to Shareholders Prior to Termination Date. Immediately prior to the Termination
Date, the board of directors of the Company shall declare a distribution to the Shareholders, pro rata in accordance with the relative number of shares of the Company’s common stock (Class A and Class B) held by each Shareholder, in an amount
equal to the Company’s estimated AAA as of the Termination Date. For purposes of this Section 2.2, the Company’s AAA shall be determined by the Chief Financial Officer of the Company in accordance with the Company’s books and
records and consistent with Section 1368 of the Code and Regulations. 
 2.3. True-Up Distribution. On or before the eleven
(11) month anniversary of the Termination Date, the Chief Financial Officer of the Company shall send a notice to shareholders of the Final Accumulated Adjustment Account (“Final AAA Determination”). If the Final AAA
Determination is more than the amount distributed to the Shareholders prior to the Termination Date pursuant to Section 2.2, then an additional distribution shall be made by the Company to the Shareholders within 30 days of the Final AAA
Determination. 
 ARTICLE 3 

TAX RETURNS AND REPORTING 

3.1. Consistent Reporting by the Company. For all taxable periods during which the Company was classified as an S Corporation, the
Company shall not (except as required by law), without the consent of the Shareholders (which consent shall not be unreasonably withheld), file any amended income tax return or change any election or accounting method with respect to the Company, if
such filing or change would increase any federal, state, local (including but not limited to city or county) or foreign income tax liability including interest and penalties, if any (collectively “Tax Liability”) of the Shareholders
for any taxable period during which the Company was classified as an S Corporation. 
 3.2. Responsibility for Tax Returns. The
Company shall file all tax returns required to be filed by the Company with respect to all periods for which returns shall become due after the closing of the Company’s Public Offering, including all returns for the S Short Year. 

  
 3 

 3.3. Responsibility for Taxes. Subject only to the indemnities set forth in Article 4,
each Shareholder shall file all required tax returns reporting such Shareholder’s allocable share of the Company’s taxable income, gain, loss, deduction, or credit for all tax periods (or any portion of a tax period) during which the
Company was an S Corporation and shall pay any and all taxes such Shareholder is required to pay as a result of being a Shareholder of the Company, for all taxable periods (or any portion of a tax period) during which the Company was an
S Corporation. For all tax periods (or any portion of a tax period) prior to the Termination Date, no Shareholder shall (except as required by law), without the consent of the Company (which consent shall not be unreasonably withheld), file an
amended individual or trust income tax return, as the case may be, which results in tax reporting by such Shareholder inconsistent with the Schedule K-1 or other tax information provided to the Shareholder by the Company, if such filing by such
Shareholder would increase the Tax Liability of the Company after the Termination Date. 
 3.4. Short Taxable Years. The parties
acknowledge that the taxable year in which the S Corporation status of the Company is terminated will be an “S Termination Year” for tax purposes, as defined in Section 1362(e)(4) of the Code. Pursuant to
Section 1362(e)(1) of the Code, the S Termination Year of the Company shall be divided into two short taxable years: an “S Short Year” and a “C Short Year.” As defined in Section 1362(e)(1)(A) of the Code,
the S Short Year shall be that portion of the Company’s S Termination Year ending on the day immediately preceding the Termination Date. Pursuant to Section 1362(e)(1)(B) of the Code, that portion of the S Termination Year beginning
on the Termination Date and ending on the last day of the taxable year shall be the C Short Year of the Company. 
 3.5. Pro Rata
Allocation. The Company and the Shareholders agree that for tax purposes (including for purposes of determining the Company’s S Corporation Taxable Income for its S Short Year) the Company shall allocate its calendar year items of income,
gain, loss, deduction and credit between the S Short Year and the C Short Year in accordance with the pro rata method of allocation (also referred to as the “per share per day method”) as set forth in Section 1362(e)(2) of the Code;
provided, however, if there is a sale or exchange of fifty percent (50%) or more of the Company’s common stock (Class A and Class B) during the S Termination Year, the Company shall allocate its calendar year items of income,
gain, loss, deduction and credit between the S Short Year and the C Short Year pursuant to normal tax accounting rules (also referred to as the “closing of the books method”) as required pursuant to Section 1362(e)(6)(D)
such that tax items shall be allocated to the S Short Year as if the tax year of the Company ended on the day before the Termination Date and to the C Short Year as if the Company’s tax year commenced on the Termination
Date. 
 ARTICLE 4 

INDEMNIFICATION 
 4.1.
Indemnification of Shareholders. 
 4.1.1. Indemnification for Tax Liability. The Company hereby agrees to indemnify and hold
the Shareholders harmless from, against and in respect of any Tax Liability, calculated at the Highest Rate, incurred by them resulting from a Final Determination of an adjustment (by reason of a Tax Proceeding) to the Company’s taxable income
which is the result of an increase or change in character of the Company’s income during the period it was treated as an S Corporation. 

  
 4 

 4.1.2. Payment to Shareholders. Any payments or other distributions made to the
Shareholders pursuant to Section 4.1.1 shall be made pro rata in accordance with the relative number of shares of the Company’s common stock (Class A and Class B) held by each Shareholder as of the last day of any applicable period. To the
extent practicable and to the extent consistent with applicable law, payments or other distributions made to the Shareholders pursuant to Section 4.1.1 will be treated as Post-Termination Distributions for U.S. federal income tax purposes. 

4.1.3. Tax Adjustment. In the event that an indemnification payment pursuant to Section 4.1.1 exceeds the amount of the increase
in the Company’s AAA resulting from the adjustment (or to the extent such payment to the Shareholders does not qualify as a Post-Termination Distribution during the Post-Termination Transition Period) such amount shall be increased by an amount
calculated pursuant to Section 4.1.5 below. 
 4.1.4. Fees and Costs. The Company hereby agrees to reimburse the Shareholders
for such professional fees or other costs as are reasonably necessary: 
 (i) to defend the Shareholders in the event of an
audit or review of the Shareholders’ income tax returns during a year in which the Shareholders were reporting the Company’s income by virtue of the Company’s S Corporation election; and 

(ii) to prepare and file amended income tax returns on behalf of the Shareholders in the event of an audit or review of the
Company’s income tax returns for any tax period, the result of which relates to an item of Company income, gain, loss, deduction, or credit reported on the Shareholders’ income tax returns for a year in which the Shareholders were
reporting the Company’s income by virtue of the Company’s S Corporation election. 
 Such reimbursement shall be limited to reasonable and
documented professional fees and costs proximately related to an audit or review of the Company’s income, gain, loss, deduction, or credit as reported on the Shareholders’ income tax returns or any amendment of the Shareholders’
income tax returns related to an audit or review of the Company’s taxable income. 
 4.1.5. Gross Up for Additional Tax. In all
events, and to the extent not otherwise reimbursed, the Company hereby agrees that if any payment pursuant to Section 4.1.1 is deemed to be taxable income to the Shareholders, the amount of such payment to the Shareholders shall be increased by
an amount necessary to equal the Shareholders’ additional Tax Liability, calculated at the Highest Rate, related to such amount (including, without limitation, any taxes on such additional amounts) so that the net amount received and retained
by the Shareholders after payment by the Shareholders of all taxes associated with the payment is equal to the payment otherwise required to be made. 

4.1.6. Payment. Any indemnification payment required to be made pursuant to this Section 4.1 shall be made within thirty
(30) calendar days after receipt of written notice from the Shareholders, or representative thereof, that a Final Determination has occurred and a payment is due by the Shareholders to the appropriate taxing authority. 

  
 5 

 4.2. Indemnification of the Company. 

4.2.1. Indemnification for Failure to Qualify as an S Corporation. The Shareholders severally (according to the relative percentage of
the outstanding shares of the Company’s common stock (Class A and Class B) owned by each Shareholder on the last day of any applicable period to which a liability described below relates) and not jointly, each hereby agree to indemnify and hold
the Company harmless from, against, and in respect of any Tax Liability, if any, calculated at the Company’s Highest Rate, resulting from the Company failing to qualify as an S Corporation under Section 1361(a)(1) of the Code (as enacted
and in effect prior to the Termination Date), pursuant to a Final Determination (by reason of a Tax Proceeding), for any taxable year on or before the Termination Date as to which the Company filed or files tax returns claiming status as an S
Corporation. 
 4.2.2. Indemnification for Tax Liability. In addition to the indemnification obligation provided in
Section 4.2.1, the Shareholders severally (according to the relative percentage of the outstanding shares of the Company’s common stock (Class A and Class B) owned by each Shareholder on the last day of any applicable period to which a
liability described below relates) and not jointly, each hereby agree to indemnify and hold harmless the Company against any increase resulting from a Final Determination of an adjustment (by reason of a Tax Proceeding) in the Company’s Tax
Liability, calculated at the Company’s Highest Rate, with respect to any tax year to the extent such increase results in a related decrease in the Tax Liability of the Shareholders for any period prior to the termination of the Company’s
status as an S Corporation. 
 4.2.3. Gross Up For Additional Tax. In all events, and to the extent not otherwise reimbursed, the
Shareholders hereby agree that if any payment pursuant to Section 4.2.2 is deemed to be taxable income to the Company, the amount of such payment shall be increased by an amount necessary to equal the Company’s additional Tax Liability
related to such amount (including, without limitation, any taxes on such additional amounts) so that the net amount received and retained by the Company after payment by the Company of all taxes associated with the payment is equal to the payment
otherwise required to be made. 
 4.2.4. Indemnification Limits. Notwithstanding anything to the contrary in this Agreement, the
Company shall not be entitled to indemnification pursuant to Sections 4.2.1, 4.2.2, and 4.2.3 until such time as the aggregate amounts calculated under Sections 4.2.1, 4.2.2, and 4.2.3 exceed One Million Dollars ($1,000,000), and then the obligation
to provide indemnification thereunder shall be for the aggregate amounts calculated under Sections 4.2.1, 4.2.2, and 4.2.3; provided, however, the Company shall not be entitled to indemnification payments pursuant to Sections 4.2.1,
4.2.2, and 4.2.3 in excess of the amount of the Shareholders’ actual income tax savings assuming the Shareholder files for all available income tax refunds attributable to the circumstances giving rise to the increase in the Tax Liability of
the Company (for the avoidance of doubt, in the absence of cooperation from a Shareholder in filing for such income tax refunds, such tax refunds shall be calculated by the Company applying the Highest Rate to the Shareholder’s items of income,
loss or deduction arising from the Company during the S Corporation taxable year to which the refund is attributable). 
 4.2.5.
Payment. The Company shall notify the Shareholders in writing within thirty (30) calendar days of a Final Determination that triggers the Shareholders’ obligation to make an 

  
 6 

 
indemnification payment to the Company pursuant to this Section 4.2. Each Shareholder shall pay to the Company such Shareholder’s share of any such indemnification payment as determined
pursuant to this Section 4.2 on the earlier of (i) thirty (30) calendar days after the Shareholder’s receipt of all anticipated income tax refunds from the applicable tax authorities, or (ii) one (1) year after receipt
of the written notice from the Company set forth above. 
 4.3. Refunds. If the Company receives a refund of any income tax
(including penalties and interest) for any period prior to the Termination Date, or as to which it has previously been indemnified by the Shareholders, the Company shall pay an amount equal to such refund, within 30 days after receipt thereof, to
the Shareholders in accordance with the percentage of the outstanding shares of the Company’s common stock (Class A and Class B) owned by each such Shareholder on the last day of any applicable period to which the refund relates. If the
Shareholders receive a refund of any income tax (including penalties and interest) as to which they have previously been indemnified by the Company, they shall, within 30 days after receipt thereon, remit an amount equal to such refund to the
Company, as appropriate. 
 4.4. Notice and Control of Tax Proceedings. Each of the Company and the Shareholders agree that within 10
days of receiving written notice of any Tax Proceeding or related matters that may affect in any way the income tax liability of a party under this Agreement, such person shall provide written notice thereof to each other party hereto. The Company
shall be entitled to handle, control and compromise or settle the defense of any such Tax Proceeding involving the Company, and each Shareholder shall be entitled to handle, control and compromise or settle the defense of any such Tax Proceeding
involving such Shareholder’s personal tax return. The applicable party or parties controlling the Tax Proceeding shall keep the other party(ies) apprised of the status thereof and shall consult with such other party(ies) concerning the conduct
of the defense thereof. Notwithstanding the foregoing, however, no party may take any action that could adversely affect the tax liability of another party without such other party’s prior written consent, which shall not be unreasonably
withheld. The parties hereto shall execute all instruments required to effectuate the provisions of this Section 4.4. 
 4.5.
Cooperation. The parties will make available to one another, as reasonably requested, and to any taxing authority, all information, records or documents relating to the liability for taxes covered by this Agreement and will preserve any such
information, records or documents until the expiration of the applicable statute of limitations or extensions thereof. The party requesting such information shall reimburse the other party for all reasonable out-of-pocket costs incurred in producing
such information. 
 4.6. Inconsistent Reporting. If a Shareholder hereafter reports an item on such Shareholder’s income tax
return in a manner inconsistent with the tax treatment reflected in the Schedule K-1 or other tax information provided to the Shareholder by the Company for a taxable period during which the Company was treated as an S Corporation, such Shareholder
shall notify the Company of such treatment before filing such Shareholder’s income tax return. If such Shareholder fails to notify the Company of such inconsistent reporting, such Shareholder shall be liable to the Company for any losses, costs
or expenses (including reasonable attorneys’ fees) arising from such inconsistent reporting, including an audit. 

  
 7 

 ARTICLE 5 

MISCELLANEOUS 
 5.1.
Counterparts. This Agreement may be executed in counterparts, each of which shall be deemed an original, but all of which counterparts collectively shall constitute an instrument representing the Agreement between the parties hereto. 

5.2. Construction of Terms. Nothing herein expressed or implied is intended, or shall be construed, to confer upon or give any person,
firm or corporation, other than the parties hereto or their respective successors, any rights or remedies under or by reason of this Agreement. 

5.3. Intent of Parties. It is the parties’ intent that the liability for income taxes arising from the operations of the Company
will be borne by the Shareholders for all periods through and including the S Short Year and by the Company for periods beginning with the C Short Year, and this Agreement shall be construed so as most equitably to achieve such intent. 

5.4. Governing Law. This Agreement between the parties hereto shall be governed by and construed in accordance with the substantive
laws of the State of Wisconsin without regard to its choice of law rules. 
 5.5. Severability. In the event that any one or more of
the provisions of this Agreement shall be held to be illegal, invalid or unenforceable in any respect, the same shall not in any respect affect the validity, legality or enforceability of the remainder of this Agreement, and the parties shall use
their best efforts to replace such illegal, invalid or unenforceable provisions with an enforceable provision approximating, to the extent possible, the original intent of the parties. 

5.6. Notices. Unless otherwise provided, any notice required or permitted under this Agreement shall be given in writing and shall be
deemed effectively given upon personal delivery or electronic communication (receipt confirmed, with a copy to be sent by reputable overnight courier as set forth herein) to the party to be notified, or one business day after delivery to a reputable
overnight courier, postage prepaid, and addressed to the party to be notified at the address indicated for such party in the Company’s records, or at such other address as such party may designate by ten (10) days, advance written notice
to the other parties. 
 5.7. Amendments and Waivers. Any term of this Agreement may be amended, and the observance of any term of
this Agreement may be waived (either generally or in a particular instance and either retroactively or prospectively), only with the written consent of each of the parties hereto. 

5.8. Full Understanding and Role of Godfrey & Kahn, S.C. Each Shareholder represents and agrees that such Shareholder fully
understands his, her or its right to discuss all aspects of this Agreement with such Shareholder’s own counsel, and that to the extent, if any, that the Shareholder desired, has availed himself, herself or itself of such right. Each Shareholder
further represents that he/she/it has carefully read and fully understands all of the provisions of this Agreement, that such Shareholder is competent to execute this Agreement, that the Shareholder’s agreement to execute this Agreement has not
been obtained by any duress and that he/she/it freely and voluntarily enters into it, and that he/she/it has read this document in its entirety and fully understands the meaning, intent and consequences of this document. This

  
 8 

 
Agreement has been drafted by Godfrey & Kahn, S.C. as counsel for the Company and for the following Shareholders: Stephen L. Schlecht, Stephen L. Schlecht & Marianne M.
Schlecht Descendants Trust, and Richard W. Schlecht. Each Shareholder, other than Stephen L. Schlecht, Stephen L. Schlecht & Marianne M. Schlecht Descendants Trust, and Richard W. Schlecht, acknowledges and agrees that
Godfrey & Kahn, S.C. has not represented such Shareholder in any way in connection with this Agreement and a conflict may exist between such Shareholder’s interest and the interests of the Company and the other Shareholders. 

[Signature Pages Follow] 

  
 9 

 IN WITNESS WHEREOF, the parties have executed this S Corporation Termination, Tax Allocation and
Indemnification Agreement on the date first set forth above. 
  

									
	 COMPANY:
  

DULUTH HOLDINGS INC.,
 a Wisconsin corporation
	 		 		 	SHAREHOLDERS:
		 		 		 		 	Stephen L. Schlecht
					
	By:	 	 	 		 		 	 DAVID T. ZENTMYER AND
 CARLA A.
ZENTMYER
 REVOCABLE TRUST

		 		 		 
		 		 		 		 
					
		 		 		 		 	 
		 		 		 		 	David T. Zentmyer, Trustee
					
		 		 		 		 	 
		 		 		 		 	Carla A. Zentmyer, Trustee
					
		 		 		 		 	 
		 		 		 		 	Carol A. Mueller
					
		 		 		 		 	 STEPHEN L. SCHLECHT &
 MARIANNE M.
SCHLECHT
 DESCENDANTS TRUST

					
		 		 		 		 	 
		 		 		 		 	John Dickens, Co-Trustee
					
		 		 		 		 	 WILLIAM E. FERRY
 REVOCABLE TRUST

					
		 		 		 		 	 
		 		 		 		 	William E. Ferry, Trustee
					
		 		 		 		 	 JULIA SCOTT FERRY
 REVOCABLE TRUST

					
		 		 		 		 	 
		 		 		 		 	Julia Scott Ferry, Trustee

  
 10 

									
					
		 		 		 		 	 
		 		 		 		 	Kelly J. Martin
					
		 		 		 		 	 
		 		 		 		 	 Thomas G. Folliard

					
		 		 		 		 	 
		 		 		 		 	Thomas Wenstrand
					
		 		 		 		 	 
		 		 		 		 	James M. Burke
					
		 		 		 		 	 
		 		 		 		 	Joan T. Brown
					
		 		 		 		 	 
		 		 		 		 	Suzanne Harms
					
		 		 		 		 	 
		 		 		 		 	Stephanie L. Pugliese
					
		 		 		 		 	 
		 		 		 		 	David Finch
					
		 		 		 		 	 
		 		 		 		 	Roger Lewis

  
 11 

  

							
				
		 		 		 	 
		 		 		 	Mark DeOrio
				
		 		 		 	 WILLIAM E. FERRY
 IRREVOCABLE TRUST OF

2013

				
		 		 		 	 
		 		 		 	 Julia Scott Ferry, Trustee

				
		 		 		 	 E. DAVID COOLIDGE, III
 ANNUITY
TRUST

				
		 		 		 	 
		 		 		 	E. David Coolidge III, Trustee
				
		 		 		 	 
		 		 		 	Allen Dittrich
				
		 		 		 	 
		 		 		 	Harry S. Schutte III
				
		 		 		 	 
		 		 		 	Barbara Wagner
				
		 		 		 	 
		 		 		 	Robert C. Malkovich, Jr.
				
		 		 		 	 
		 		 		 	Kathleen A. Jack

  
 12 

							
				
		 		 		 	 
		 		 		 	Joan K. Conlin
				
		 		 		 	 
		 		 		 	Mark R. Pickart
				
		 		 		 	 
		 		 		 	Richard W. Schlecht
				
		 		 		 	 
		 		 		 	Timothy J. Balliet

  
 13

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