Document:

EX-10.8

 Exhibit 10.8 

DULUTH HOLDINGS INC. 

RESTRICTED STOCK AGREEMENT 

THIS RESTRICTED STOCK AGREEMENT (the “Agreement”) is made and entered into as of the 2nd day of February, 2015, by and between
DULUTH HOLDINGS INC., a Wisconsin corporation (the “Company”), and AI Dittrich (the “Executive”). 
 WITNESSETH: 

WHEREAS, the Executive is a key employee of the Company and in order to provide the Executive with incentives to remain employed by the
Company and to advance the interests of the Company, the Board of Directors of the Company has determined that it is in the best interest of the Company to provide the Executive with an opportunity to obtain shares of the Company’s common stock
on the terms and conditions provided herein; and 
 WHEREAS, the purpose of this Agreement is to set forth the terms and conditions pursuant
to which the Subject Shares (as hereinafter defined) are being transferred to the Executive. 
 NOW, THEREFORE, in consideration of the
mutual promises hereinafter set forth, and other good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, and conditioned upon Executive’s execution of a Restrictive Covenant Agreement, the parties hereto
promise and agree as follows: 
 1. Award of Subject Shares. Subject to Section 9, below, the Executive’s agreements herein,
and conditioned upon the Executive’s execution of the Restrictive Covenant Agreement delivered simultaneously with this Agreement and incorporated herein, the Company hereby awards shares of the Company’s Class B non-voting common
stock (the “Common Stock”) to the Executive, subject to the terms and conditions set forth in this Agreement. The award shall consist of sixty-six (66) shares of the Common Stock (the “Subject Shares”). 

2. Vesting of the Subject Shares. The Subject Shares shall vest as follows: 

 

									
	 Vesting Date
	  	Number of Subject Shares
Vested	 	  	Cumulative Number of
Subject Shares Vested	 
	 February 1, 2017
	  	 	33	  	  	 	33	  
	 February 1, 2018
	  	 	33	  	  	 	66	  

 3. Unvested Shares Upon Termination and Change in Control. In the event that the Executive’s
employment with the Company is terminated for any reason, all vesting of the subject shares shall immediately cease. Any of the Subject Shares which have not become vested shall be referred to herein as “Unvested Stock.” In the event the
Executive’s employment with the Company is terminated for any reason, the Executive shall forfeit all Unvested Stock and all of such Unvested Stock shall revert to the Company. All Unvested Stock that has not

 
been previously forfeited shall be deemed to be fully vested upon a Change in Control. Change in Control shall mean (i) a sale, transfer or other disposition of all or substantially all of
the assets of the Company, whether consummated in one transaction or a series of related transactions; or (ii) a sale, transfer or other disposition of a majority interest in all of the issued and outstanding capital stock of the Company,
including, without limitation, pursuant to a plan of merger, share exchange or consolidation, to an “Unrelated Purchaser(s).” “Unrelated Purchaser(s)” shall mean (i) any entity which is not directly or indirectly, actually
or constructively, an affiliate of or controlled by any of the following: the Company, a subsidiary of the Company or an affiliate of the Company or (ii) any person who is not a stockholder or a member or members of a group consisting of a
stockholder’s spouse, issue or a trust created for the primary benefit of the stockholder, his or her spouse or his or her issue. 
 4.
Shareholder Status. Prior to the vesting of the Subject Shares, but only so long as the Executive remains employed by the Company, the Executive shall have (i) the right to vote the Subject Shares on certain matters which the Wisconsin
Business Corporation Law provides that all stock, whether voting or non-voting, must be given the right to vote, (ii) the right to receive and retain all regular cash dividends paid or distributed in respect of the Subject Shares if the record
date for such dividends is on or after the date of this Agreement (provided that the Executive has properly executed and filed an election under Section 83(b) of the Internal Revenue Code related to the grant of the Subject Shares), and
(iii) except as expressly provided otherwise herein, all other rights as a holder of outstanding shares of the Common Stock. Until the Subject Shares fully vest pursuant to Section 2, above, the Company shall retain custody of the stock
certificates representing the Subject Shares. As soon as practicable after all of the Subject Shares vest, the Company shall release or cause to be released certificate(s) representing such shares. Notwithstanding the foregoing, the Company shall
have the right to delay the delivery of any such shares to be delivered hereunder until (a) the completion of such registration or qualification of the shares under federal, state or foreign law, ruling or regulation as the Company shall deem
to be necessary or advisable, and (b) receipt from the Executive of such documents and information as the Company may deem necessary or appropriate in connection with such registration or qualification or the delivery of the Subject Shares
hereunder. 
 5. Stockholders Agreement. By execution of this Agreement, the Executive agrees that the Executive and the Subject
Shares shall be bound by the terms and restrictions of the Amended and Restated Stockholders Agreement dated as of December 17, 2001, as amended from time to time among the Company and others (the “Stockholders Agreement”) as if such
Executive were an original party thereto. As a condition to the award of the Subject Shares hereunder, the Executive shall execute the Joinder Agreement to the Stockholders Agreement and if applicable, the Spousal Consent and Acknowledgment, each
dated as of even date herewith. Both forms are attached hereto as Exhibit A. 
 6. Warranties of the Executive. The Executive
hereby warrants and represents to the Company, which warranties and representations shall be true and correct as of the date hereof and which shall survive the date hereof, as follows: 

(a) The Executive has all necessary power and authority to execute and deliver this Agreement and to comply with the provisions
hereof; 

 (b) The execution, delivery and performance of this Agreement and the agreements
and instruments relating hereto by the Executive constitute the valid and legally binding obligations of the Executive, enforceable against the Executive in accordance with their respective terms; 

(c) Neither the execution and delivery of this Agreement by the Executive, nor the consummation of the transactions hereby,
will violate or constitute a breach of any agreement, instrument or restriction to which the Executive is a party or by which the Executive is bound; 

(d) That (i) the Executive is accepting the Subject Shares solely for the Executive’s own account for investment and
not on behalf of other persons or with a view to the distribution or resale thereof; (ii) the Executive’s financial condition is such that the Executive is not under any present necessity or constraint to dispose of the Subject Shares to
satisfy any existing or contemplated debt or undertaking; (iii) the Executive has no present or contemplated agreement, understanding, arrangement, obligation, indebtedness or commitment providing for or which is likely to provide for a
disposition in any manner of the Subject Shares and is not aware of any circumstances presently in existence which are likely to promote in the future any disposition by the Executive of the Subject Shares; and (iv) the Executive does not have
in mind any sale of the Subject Shares upon the occurrence or nonoccurrence of any predetermined or undetermined event or circumstance; and 

(e) That (i) the Executive is aware that the Subject Shares have not been registered (nor is registration contemplated)
under the Securities Act of 1933, as amended (the “Act”), and accordingly, that federal and state securities laws require that the Subject Shares be held indefinitely unless they are subsequently registered under such Act or unless, in the
opinion of counsel for the Company, a sale or transfer may be made without registration thereunder; (ii) the Executive fully understands that the Company is under no obligation, and has not given any commitment whatsoever, to register the
Subject Shares or the sale thereof under the Act; (iii) the Executive acknowledges and agrees that the Executive has had access to sufficient information to enable the Executive, because of the Executive’s knowledge and experience in
financial and business matters, to evaluate the risks of this investment and to make an informed decision; (iv) the Executive further understands that the Executive must bear the economic risk of the Executive’s investment in the Subject
Shares for an indefinite period of time; and (v) the Executive agrees that the Subject Shares may bear a legend restricting the transfer thereof consistent with the foregoing. 

7. Warranties of the Company. The Company hereby warrants and represents to the Executive, which warranties and representations shall
be true and correct as of the date hereof and which shall survive the Closing, as follows: 
 (a) The Company has all
necessary power and authority to execute and deliver this Agreement and the agreements and instruments relating hereto and to comply with the provisions hereof; 

 (b) The execution, delivery and performance of this Agreement and the agreements
and instruments relating hereto by the Company constitute the valid and legally binding obligations of the Company, enforceable against it in accordance with their respective terms; 

(c) Neither the execution and delivery of this Agreement by the Company, nor the consummation of the transactions hereby, will
violate or constitute a breach of any agreement, instrument or restriction to which it is a party or by which it is bound; and 

(d) The Subject Shares, when validly issued, will be fully paid and nonassessable. 

8. Indemnification. Each party hereto agrees to indemnify and hold harmless the other party upon demand from and against any and all
liabilities, damages, costs and expenses (including reasonable attorneys’ fees) resulting from any breach by such party of any warranty, representation or agreement hereunder. 

9. Taxes. As a condition of accepting this award, the Executive hereby agrees to complete and file an election under Section 83(b)
of the Internal Revenue Code, in the form attached hereto as Exhibit B, to treat the fair market value of the Subject Shares as taxable income for the year of the award, whether such Subject Shares are vested or not. The Executive shall
forfeit the award if he or she does not complete and file a timely election under Section 83(b) of the Internal Revenue Code. The Company shall require the payment of or withhold any income or withholding tax which it believes is payable as a
result of the award of the Subject Shares or any payments thereon or in connection therewith, and the Company may defer making delivery with respect to the Subject Shares until arrangements satisfactory to the Company have been made with regard to
any such withholding obligation. To assist the Executive with the payment of such taxes when the Executive makes the Section 83(b) election, the Company shall pay to the Executive additional compensation in the amount of $381,226.15. The
Company shall apply this amount, after deduction of appropriate withholding taxes, to the Executive’s income and withholding tax obligations resulting from the award of the Subject Shares to the Executive. 

10. No Employment Rights. This Agreement shall not confer upon the Executive any right with respect to continuation of employment by
the Company, nor shall it interfere in any way with the right of the Company to terminate the Executive’s employment at any time. 

11. Adjustments. In the event of any change in the outstanding Common Stock of the Company by reason of a stock split, stock dividend,
combination or reclassification of shares, recapitalization, merger, sale or similar event, the Company shall be authorized to adjust the Subject Shares or substitute new securities for the Subject Shares in an equitable manner. In the event of a
merger, sale or similar event in which any shares of stock of another company (the “Consideration Shares”) are received as all or part of the consideration for the issued and outstanding shares of the Common Stock, the Company shall
substitute an equitable number of the Consideration Shares for the Subject Shares. After such substitution, the Consideration Shares shall be treated the same as the Subject Shares for purposes of this Agreement and this Agreement shall continue and
remain valid in all respects. 

 12. Notices. Any notice to be given to the Company under the terms of this Agreement shall
be deemed to be given and received in all respects (i) when personally delivered, (ii) when sent via reputable overnight courier service, or (iii) three (3) days after being deposited in the United States mail, registered or
certified mail, postage prepaid, return receipt requested, in each case addressed to the address of the Executive as the same shall appear on the stock transfer book of the Company, or, in the case of the Company, the principal office of the
Company. 
 13. Pronouns; Headings. Whenever the context may require, any pronouns used in this Agreement shall include the
corresponding masculine, feminine or neuter forms, and the singular forms of nouns and pronouns shall include the plural, and vice-versa. The headings of the sections of this Agreement are for convenience of reference only and in no way define,
limit or affect the scope or substance of any section of this Agreement. 
 14. Entire Agreement. This Agreement constitutes the
entire agreement between the parties and supersedes all prior agreements and understandings, whether written or oral, relating to the subject matter of this Agreement. 

15. Amendment. This Agreement may be amended or modified only by a written instrument executed by each of the parties hereto. 

16. Governing Law. This Agreement and all matters arising hereunder or in connection herewith shall be determined in accordance with
the internal laws of Wisconsin without regard to principles and conflicts of law. 
 17. Successors and Assigns. This Agreement shall
be binding upon and inure to the benefit of both parties and their respective successors and permitted assigns, including any corporation with which or into which the Company may be merged or which may succeed to its assets or business; provided,
however, this Agreement and the rights and obligations hereunder shall not be assignable or transferable by the Executive. 
 18.
Counterparts. This Agreement may be executed in one or more counterparts, each of which shall be deemed an original but all of which together shall constitute one and the same document. 

19. Tax Reimbursement. In the event that the Executive makes the Section 83(b) election and the Executive’s employment is
subsequently terminated by the Company without Cause (as defined in the Stockholders Agreement), the Company shall reimburse the Executive for one-half of the income taxes paid (at the 48% rate) in connection with the Section 83(b) election
that are attributable to any Unvested Stock (excluding any taxes paid in connection with the additional compensation) at the time of such termination. 

[Signature page and exhibits follow] 

 IN WITNESS WHEREOF, the parties have caused this Agreement to be effective as of the date first
written above. 
  

			
	COMPANY:
	
	DULUTH HOLDINGS INC.
		
	By:	 	/s/ Stephen L. Schlecht
		 	Stephen L. Schlecht, Executive Chairman
	
	EXECUTIVE:
	
	/s/ Al Dittrich
	Al DittrichEX-10.9

 Exhibit 10.9 

RESTRICTIVE COVENANT AGREEMENT 

 

 THIS RESTRICTIVE COVENANT AGREEMENT (“Agreement”) is made and entered into by and
between Stephanie Pugliese (“Executive”) and Duluth Holdings, Inc. (the “Company”). 
 RECITALS 

A. As a condition of and in consideration for the Company’s award of common stock to Executive pursuant to that certain Restricted Stock
Agreement dated February 2, 2015, Executive has agreed to execute and be bound by the terms of this Agreement. 
 B. During
Executive’s employment with the Company, Executive has personally generated and been entrusted with, and will continue to personally generate and be entrusted with, information, ideas and materials which are the Company’s confidential and
proprietary property, including, without limitation, trade secrets, confidential financial information, product designs, product costs, marketing information and information related to other confidential and proprietary matters of the Company. 

C. The Company has expended and will continue to expend substantial time, effort and money to protect such confidential and proprietary
Company property, to service its customers and prospective customers and to provide Executive the opportunity and the resources to extend the goodwill of the Company. 

D. By entering into this Agreement, Executive acknowledges and agrees that the scope of the restrictions contained in this Agreement are
appropriate, necessary and reasonable for the protection of the Company’s business, goodwill, and property rights, including the protection of the Company’s confidential and proprietary property and its customer relationships. 

E. By entering into this Agreement, Executive further acknowledges and agrees that the restrictions imposed by this Agreement will not prevent
him/her from earning a living in the event of, and after, the end, for whatever reason, of his/her employment with the Company. 

AGREEMENT 
 In
consideration of the award of common stock and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, Executive and the Company hereby agree as follows: 

1. Confidentiality Obligations. 

1.1 During Employment. While Executive is employed by the Company, Executive will not directly or indirectly use or disclose any
Confidential Information or Trade Secret of the 

 Company, except in the interest and for the benefit of the Company. 

1.2 Trade Secrets Post-Employment. After the end, for whatever reason, of Executive’s employment with the Company,
Executive will not directly or indirectly use or disclose any Trade Secret of the Company. 
 1.3 Confidential Information
Post-Employment. For a period of two (2) years following the end, for whatever reason, of Executive’s employment with the Company, Executive will not directly or indirectly use or disclose any Confidential Information of the Company.

 1.4 General Skills and Knowledge. Nothing in this Agreement shall prevent Executive, after the end of employment with the
Company, from using general skills and knowledge gained while employed by the Company. 
 1.5 Trade Secret Law. Nothing in
this Agreement shall limit or supersede any common law, statutory or other protections of trade secrets where such protections provide the Company with greater rights or protections for a longer duration than provided in this Agreement. 

2. Non-Competition During Employment. While Executive is employed by the Company, Executive will not directly or indirectly compete
against the Company, or directly or indirectly divert or attempt to divert business from the Company anywhere the Company does business. 

3. 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. 

4. 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 his/her employment with the Company or solicit such an individual for employment outside the Company in a manner that would end or diminish that
employee’s services to the Company. 
 5. Business Idea Rights. 

5.1 Assignment. The Company will own, and Executive hereby assigns and agrees to assign to the Company, all rights in all
Business Ideas which Executive originates or develops either 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.

 

 5.2 Disclosure. While employed by the Company, Executive will promptly disclose
all Business Ideas to the Company. 
 5.3 Execution of Documentation. Executive, at any time during or after the term of
his/her employment with the Company may reasonably require to perfect its patent, copyright and other rights to such Business Ideas throughout the world. 

6. Return of Property. Upon the end, for whatever reason, of Executive’s employment with the Company or upon request by the
Company at any time, Executive shall immediately return to the Company all property, documents, records, and materials belonging and/or relating to the Company, all pass- words and/or access codes to such
Company property, and all copies of all such materials. Upon the end, for whatever reason, of Executive’s employment with the Company or upon request by the Company at any time, Executive further agrees to destroy such records maintained by
him/her on his/her own computer equipment and to certify in writing, at the Company’s request, that such destruction bas occurred. 

7. Definitions. 
 7.1
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. 

7.2 Trade Secret. The term “Trade Secret” has that meaning set forth under applicable law. 

7.3 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 him/her prior to his/her 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 his/her employment without
use of Confidential Information or Trade Secrets of the Company. 
 7.4 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. 

7.5 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 and (ii) had combined annual revenues in excess of $100 million. 

7.6 Territory. The term “Territory” shall mean the United States of America and Canada. 

7.7 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. 
 8. Executive Disclosures and
Acknowledgments. 
 8.1 Confidential Information of Others. Executive certifies that Executive has not, and will not,
disclose or use during Executive’s time as an employee of the Company, any confidential information which Executive acquired as a result of any previous employment or under a contractual obligation of confidentiality or secrecy before Executive
became an employee of the Company. All prior obligations (written and oral), such as confidentiality agreements or covenants restricting future employment or consulting, that Executive has entered into which restrict Executive’s ability to
perform any services as an employee for the Company are listed below under the heading List of Prior Obligations. 

 

  
 2 

 
 8.2 Prospective Employers. Executive agrees, during the term of any restriction
contained in this Agreement, to disclose this Agreement to any entity which offers employment to Executive. Executive further agrees that the Company may send a copy of this Agreement to, or otherwise make the provisions hereof known to, any of
Executive’s potential or future employers. 
 9. Miscellaneous. 

9.1 Binding Effect. This Agreement binds Executive’s heirs, executors, administrators, legal representatives and assigns
and inures to the benefit of the Company and its successors and assigns. 
 9.2 Entire Agreement; Amendment or Waiver. This
Agreement contains the entire understanding between the parties with respect to the subject matter hereof, and all prior discussions, negotiations, agreements, correspondence and understandings, whether oral or written, between Executive and the
Company with respect to the subject matter addressed in this Agreement are merged in it and superseded by it. No provision of this Agreement may be amended or waived other than in writing by the party against whom enforcement of such amendment or
waiver is sought. 
 9.3 Injunctive Relief. The parties agree that damages will be an inadequate remedy for breaches of this
Agreement and in addition to damages and any other available relief, a court shall be empowered to grant injunctive relief (without the necessity of posting bond or other security). 

9.4 Governing Law. This Agreement shall be governed by and construed in accordance with the substantive and procedural laws of
Wisconsin. 
 9.5 Consideration. Execution of this Agreement is a condition of Executive’s award of common stock pursuant
to that certain Restricted Stock Agreement dated February 2, 2015 and constitutes the consideration for Executive’s undertakings hereunder. Executive acknowledges and agrees that execution of this Agreement is not a condition of
Executive’s continued employment with the Company. 
 9.6 Severability. The obligations imposed by, and the provisions of
this Agreement are severable and should be construed independently of each other. The invalidity of one provision shall not affect the validity of any other provision.

 9.7 Terminable-At-Will. Nothing in this Agreement shall be construed to limit the
right of either party to terminate the employment relationship at any time for any or no reason with or without notice. 
 9.8
Jurisdiction and Venue. Executive and the Company agree that all disputes between them regarding this Agreement, including, without limitation, all disputes involving claims for interpretation, breach or enforcement of this Agreement,
shall be litigated exclusively in the State of Wisconsin Circuit Court for Dane County or the United States District Court for the Western District of Wisconsin, and both parties irrevocably consent to, and waive any challenge to, the jurisdiction
of, and venue in, such courts. 
 List of Prior Obligations 

 

	
	 
	
	 
	
	 

  

			
	 EXECUTIVE:

	
	 /s/ Stephanie Pugliese

	  

Date: February 2, 2015

	
	 DULUTH HOLDINGS, INC.

		
	 By:
	 	 /s/ Mark DeOrio

	  
 Date: February 2,
2015

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