As filed with the Securities and Exchange Commission on February 8, 2024

Registration No. 333-   

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM S-8

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

Duluth Holdings Inc.

(Exact name of registrant as specified in its charter)

Inducement Restricted Stock Award Agreement

(Full title of the plan)

Samuel M. Sato

President and Chief Executive Officer

Duluth Holdings Inc.

201 East Front Street

Mount Horeb, Wisconsin 53572

(Name and address of agent for service)

(608) 424-1544

(Telephone number, including area code, of agent for service)

with copy to:

Dennis F. Connolly

Godfrey & Kahn, S.C.

833 East Michigan Street

Suite 1800

Milwaukee, WI 53202-5615

(414) 273-3500

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

EXPLANATORY NOTE

This registration statement on Form S-8 (the “Registration Statement”) is filed by Duluth Holdings Inc. (the “Registrant” or the “Company”), relating to the registration of shares of Class B common stock (the “Common Stock”) of the Registrant to be granted to Heena Agrawal, Chief Financial Officer of the Registrant, pursuant to the terms of an Inducement Restricted Stock Award Agreement to be dated on or about February 12, 2024 (the “Plan”), as an inducement material to the executive entering into employment with the Registrant.

PART I

INFORMATION REQUIRED IN THE SECTION 10(a) PROSPECTUS

The documents containing the information specified in Part I of the Instructions to the Registration Statement on Form S-8 will be sent or given to the participant in the Plan covered by this Registration Statement, as applicable and as required by Rule 428(b)(1) promulgated under the Securities Act of 1933, as amended (the “Securities Act”). Such documents need not be filed with the Securities and Exchange Commission (the “SEC”) either as part of this Registration Statement or as prospectuses or prospectus supplements pursuant to Rule 424. These documents and the documents incorporated by reference in the registration statement pursuant to Item 3 of Part II of this Form, taken together, constitute a prospectus that meets the requirements of Section 10(a) of the Securities Act.

PART II

INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3. Incorporation of Documents by Reference.

The Registrant hereby incorporates by reference into this Registration Statement the following documents previously filed with the Commission:

(1) The Registrant’s annual report on Form 10-K for the fiscal year ended January 29, 2023.

(2) The Registrant’s quarterly report on Form 10-Q for the quarters ended April  30, 2023, July  30, 2023 and October 29, 2023.

(3) The Registrant’s current reports on Form 8-K filed on February  24, 2023, May  31, 2023, July  24, 2023, August  31, 2023, and January 23, 2024 (provided that any portions of such reports that are deemed furnished and not filed pursuant to instructions to Form 8-K shall not be incorporated by referenced into this Registration Statement).

(4) The description of the Registrant’s Common Stock contained in the Registrant’s Registration Statement on Form S-1, as amended (Reg. No.  333-207300), which description is incorporated by reference into the Form 8-A filed with the Securities and Exchange Commission on November 17, 2015, pursuant to the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and any amendment or report filed for the purpose of further updating such description.

All documents filed by the Registrant pursuant to Sections 13(a), 13(c), 14 and 15(d) of the Exchange Act on or after the date of this Registration Statement and prior to the filing of a post-effective amendment to this Registration Statement that indicates that all securities offered have been sold or that deregisters all securities then remaining unsold shall be deemed to be incorporated by reference in this Registration Statement and to be part hereof from the date of filing of such documents; provided, however, that documents or information deemed to have been furnished and not filed in accordance with the rules of the Commission shall not be deemed incorporated by reference into this Registration Statement.

Any statement contained in a document incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes of this Registration Statement to the extent that a statement contained herein or in any subsequently filed document which also is deemed to be incorporated by reference herein modifies or supersedes such statement. Any such statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.

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Item 4. Description of the Securities

Not applicable.

Item 5. Interests of Named Experts and Counsel.

Mr. John A. Dickens and Ms. Jennifer A. Hannon, shareholders of Godfrey & Kahn, S.C., in their capacity as co-trustees of the Stephen L. Schlecht and Marianne M. Schlecht Descendants Trust, have shared voting and dispositive power over 8,694,295 shares of Class B common stock of the Company. Mr. Dickens also personally holds 7,250 shares of Class B common stock of the Company.

Item 6. Indemnification of Directors and Officers.

Sections 180.0850 to 180.0859 of the Wisconsin Business Corporation Law (the “WBCL”) require a corporation to indemnify any director or officer who is a party to any threatened, pending or completed civil, criminal, administrative or investigative action, suit, arbitration or other proceeding, whether formal or informal, which involves foreign, federal, state or local law and that is brought by or in the right of the corporation or by any other person. A corporation’s obligation to indemnify any such person includes the obligation to pay any judgment, settlement, forfeiture or fine, including any excise tax assessed with respect to an employee benefit plan, and all reasonable expenses, including fees, costs, charges, disbursements, attorney’s fees and other expenses incurred except in those cases in which liability was incurred as a result of the breach or failure to perform a duty that the director or officer owes to the corporation and the breach or failure to perform constitutes: (i) a willful failure to deal fairly with the corporation or its shareholders in connection with a matter in which the director or officer has a material conflict of interest; (ii) a violation of criminal law, unless the person has reasonable cause to believe his or her conduct was lawful or had no reasonable cause to believe his or her conduct was unlawful; (iii) a transaction from which the person derived an improper personal profit; or (iv) willful misconduct.

An officer or director seeking indemnification is entitled to indemnification if approved in any of the following manners: (i) by a majority vote of a disinterested quorum of the board of directors, or if such quorum of disinterested directors cannot be obtained, by a majority vote of a committee of two or more disinterested directors; (ii) by independent legal counsel; (iii) by a panel of three arbitrators; (iv) by an affirmative vote of disinterested shareholders; (v) by a court; or (vi) with respect to any additional right to indemnification granted, by any other method permitted in Section 180.0858 of the WBCL.

Reasonable expenses incurred by a director or officer who is a party to a proceeding may be reimbursed by a corporation at such time as the director or officer furnishes to the corporation written affirmation of his or her good faith belief that he or she has not breached or failed to perform his or her duties and a written undertaking to repay any amounts advanced if it is determined that indemnification by the corporation is not required.

The indemnification provisions of Sections 180.0850 to 180.0859 of the WBCL are not exclusive. A corporation may expand an officer’s or director’s right to indemnification (i) in its articles of incorporation or bylaws; (ii) by written agreement between the director or officer and the corporation; (iii) by resolution of its board of directors; or (iv) by resolution of a majority of all of the corporation’s voting shares then issued and outstanding.

As permitted by Section 180.0858 of the WBCL, the Company has adopted indemnification provisions in its amended and restated bylaws that are substantially similar to the statutory indemnification provisions. Additionally, the Company has purchased director and officer liability insurance.

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Item 7. Exemption from Registration Claimed.

Not applicable.

Item 8. Exhibits.

(a) The following exhibits are filed with or incorporated by reference into this Registration Statement pursuant to Item 601 of Regulation S-K:

Item 9. Undertakings.

A. The undersigned Registrant hereby undertakes:

(1) To file, during any period in which offers or sales are being made, a post-effective amendment to this registration statement:

(i) To include any prospectus required by Section 10(a)(3) of the Securities Act of 1933;

(ii) To reflect in the prospectus any facts or events arising after the effective date of the registration statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the registration statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the changes in volume and price represent no more than a 20 percent change in the maximum aggregate offering price set forth in the “Calculation of Registration Fee” table in the effective registration statement;

(iii) To include any material information with respect to the plan of distribution not previously disclosed in the registration statement or any material change to such information in the registration statement.

Provided, however, that paragraphs (A)(1)(i) and (A)(1)(ii) do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained in periodic reports filed with or furnished to the Commission by the Registrant pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 that are incorporated by reference in this registration statement.

(2) That, for the purpose of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

(3) To remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination of the offering.

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B. The undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing of the Registrant’s annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 (and, where applicable, each filing of an employee benefit plan’s annual report pursuant to Section 15(d) of the Securities Exchange Act of 1934) that is incorporated by reference in the registration statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

C. Insofar as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons of the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable. In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the Securities Act of 1933 and will be governed by the final adjudication of such issue.

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SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form S-8 and has duly caused this registration statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the Village of Mount Horeb, State of Wisconsin, on this 8th day of February, 2024.

Pursuant to the requirements of the Securities Act of 1933, as amended, this Registration Statement has been signed by the following persons in the capacities and on the dates indicated.

Exhibit 5.1

February 8, 2024

Duluth Holdings Inc.

201 East Front Street

Mt. Horeb, Wisconsin 53572

RE: Registration Statement on Form S-8 of Duluth Holdings Inc.

Ladies and Gentlemen:

We have acted as your counsel in connection with the issuance by Duluth Holdings Inc., a Wisconsin corporation (the “Company”), of up to 110,307 shares of the Company’s Class B common stock, no par value per share (the “Shares”), pursuant to the Inducement Restricted Stock Award Agreement to be entered into by and between the Company and Heena Agrawal on or about February 12, 2024 (the “Agreement”), as described in the Company’s prospectus relating to the Agreement dated February 12, 2024 (the “Prospectus”) in connection with the Company’s Registration Statement on Form S-8, to be filed with the Securities and Exchange Commission on or about February 8, 2024 (the “Registration Statement”).

We have examined: (a) the Agreement, the Prospectus and the Registration Statement, (b) the Company’s Articles of Incorporation and Bylaws, each as amended and restated to date, (c) certain resolutions of the Company’s Board of Directors, and (d) such other proceedings, documents and records as we have deemed necessary to enable us to render this opinion.

Based on the foregoing, and subject to the limitations, qualifications and assumptions set forth herein, we are of the opinion that the Shares have been duly authorized and, upon issuance in accordance with the terms of the Agreement, will be validly issued, fully paid and nonassessable.

The foregoing opinions are limited to the laws of the State of Wisconsin as currently in effect, and no opinion is expressed with respect to such laws as subsequently amended, or any other laws, or any effect that such amended or other laws may have on the opinions expressed herein. The foregoing opinions are limited to matters stated herein, and no opinion is implied or may be inferred beyond the matters expressly stated herein. The foregoing opinions are given as of the date hereof and based solely on our understanding of facts in existence as of such date after the aforementioned examination, and we undertake no obligation to advise you of any changes in applicable laws after the date hereof or of any facts that might change the opinions expressed herein that we may become aware of after the date hereof.

We consent to the filing of this opinion as an exhibit to the Registration Statement.

Exhibit 10.1

DULUTH HOLDINGS INC.

INDUCEMENT RESTRICTED STOCK AWARD AGREEMENT

This Restricted Stock Award Agreement (this “Agreement”) is executed as of February 12, 2024, by and between Duluth Holdings Inc., a Wisconsin corporation (the “Company”), and Heena Agrawal (the “Executive”). This Agreement is not subject to the 2015 Equity Incentive Plan of Duluth Holdings Inc. (the “Plan”), but all terms used in this Agreement and not otherwise defined herein shall have the same meanings as set forth in the Plan, which Plan is attached hereto as Exhibit A.

W I T N E S S E T H:

WHEREAS, the Executive is hereby granted Restricted Stock as an inducement material to her employment with the Company under NASDAQ Listing Rule 5635(c)(4), subject to the terms and conditions provided in this Agreement.

NOW, THEREFORE, the Company and the Executive hereby agree as follows:

1. Terms of Award. The Executive is hereby granted _____ shares of Class B Common Stock of the Company subject to the terms of this Agreement (the “Restricted Stock”). The Restricted Period for 50% of such shares (_____) shall end on February 12, 2024 (the “First Tranche Shares).” The Restricted Period for the remaining 50% of the shares of Restricted Stock (the “Second Tranche”) shall end February 12, 2027, the third anniversary of Executive’s first day of employment. In the event that the Executive’s employment with the Company is terminated for any reason, all vesting of the Second Tranche shall immediately cease. Any of the Restricted Stock which has 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.

2. Repayment Condition. If Executive voluntarily terminates employment or is terminated by the Company for Cause during the Repayment Period, Executive shall be required to reimburse the Company with respect to the First Tranche Shares pursuant to this Section 2. To the extent Executive, as of the last date of her employment with the Company, still holds the number of Shares corresponding to those required to be surrendered during the applicable Repayment Period (such total number of Shares, the “Repayment Share Number”) on the last day of her employment with the Company, surrender of the same number of Shares (or an adjusted amount in the event of a stock split or reverse stock split in the interim) to the Company shall be sufficient reimbursement under this Section 2 and Executive agrees hereunder to surrender such Shares. To the extent that Executive does not hold Shares equal to the Repayment Share Number as of the last date of her employment with the Company, Executive agrees to surrender of (a) the full number of Shares held by Executive as of the date of her employment with the Company plus (b) an amount in cash equal to (i) the difference between the number of Shares surrendered in (a) and the Repayment Share Number, multiplied by (ii) the amount of proceeds per Share realized (or Fair Market Value in the event of a gift by Executive) by Executive upon disposition of that same number of Shares during the Repayment Period,

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whereas in the event that tracking of the actual amount of proceeds realized per Share by Executive upon disposition of the Shares is not possible or impracticable, the maximum amounts per Share realized by Executive upon the disposition of Shares during the Repayment Period shall be used for purposes of calculating this reimbursement. In the event Executive is required to reimburse the Company pursuant to this Agreement, Executive hereby agrees to reimburse the Company pursuant to this Section 2 with immediately available funds, no later than thirty (30) days of the last day of her employment with the Company. Executive further agrees that Company may deduct amounts due the Company pursuant to this Agreement from any wages owed by Company to the Executive, to the extent permissible under Section 409A of the Code.

“Repayment Period” means:

for 100% of the First Tranche Shares, the period beginning on February 12, 2024 and ending on February 11, 2025.

for 75% of the First Tranche Shares, the period beginning on February 12, 2025 and ending on February 11, 2026.

for 50% of the First Tranche Shares, the period beginning on February 12, 2026 and ending on February 11, 2027.

3. Dividends and Voting Rights. The Executive shall be entitled to receive any dividends that become payable with respect to such shares of Restricted Stock and shall be entitled to voting rights with respect to such shares of Restricted Stock.

4. Restrictions on Restricted Stock. The Restricted Stock may not be sold, assigned, conveyed, donated, pledged, transferred or otherwise disposed of or encumbered for the Restricted Period. For the avoidance of doubt, these restrictions shall not apply to the First Tranche Shares because the Restricted Period ends on the date of this Agreement.

5. Compliance with Laws and Regulations. The issuance and transfer of Shares in accordance with this Agreement will be subject to compliance by the Company and Executive with all applicable requirements of federal and state securities laws and with all applicable requirements of any stock exchange on which Shares may be listed at the time of such issuance or transfer. The Company shall have the right to delay the issue or delivery of any Shares 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 Executive of such documents and information as the Committee may deem necessary or appropriate in connection with such registration or qualification.

6. Adjustments. The Restricted Stock granted under this Agreement shall be subject to the provisions of Section 14(a) and 17(a) of the Plan as if they had been granted thereunder in the event of the circumstances described therein.

7. Taxes. The Company may require payment or reimbursement of or may withhold any tax that it believes is required as a result of the grant or vesting of such Restricted Stock or any payments in connection with the Restricted Stock, and the Company may defer making delivery of any Restricted Stock or Shares in respect of Restricted Stock until arrangements satisfactory to the Company have been made with regard to any such payment, reimbursement, or withholding obligation. The Executive 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.

8. Complete Agreement. In the event of a conflict between the terms of this Agreement and the Offer Letter dated January 17, 2024, this Agreement shall control.

9. No Right to Service. The granting of Restricted Stock under this Agreement shall not be construed as granting to the Executive any right with respect to continued employment with the Company, nor shall it interfere in any way with the right of the Company to terminate the Executive’s employment at any time.

10. Counterparts. This Agreement may be executed in any number of counterparts, each of which shall be deemed an original, but all of which shall constitute one and the same agreement providing for a single grant of shares of Restricted Stock; and any counterpart may be delivered to another party by e-mail or facsimile transmission. A facsimile (“fax”) signature to this Agreement, or a signature to this Agreement electronically transmitted in “pdf” format or by email, shall be considered a binding signature and shall have the same force and effect as an original signature.

IN WITNESS WHEREOF, the Company has caused this Agreement to be executed as of the date and year first above written.

The undersigned Executive hereby accepts the foregoing grant of Restricted Stock and agrees to the several terms and conditions hereof.

Exhibit 23.2

		KPMG LLP Suite 1050 833 East Michigan Street Milwaukee, WI 53202-5337

Consent of Independent Registered Public Accounting Firm

We consent to the use of our reports dated January 29, 2023, with respect to the consolidated financial statements of Duluth Holdings Inc., and the effectiveness of internal control over financial reporting, incorporated herein by reference.

/s/ KPMG

Milwaukee, Wisconsin

February 8, 2024

Exhibit 24.1

POWER OF ATTORNEY

(Registration Statement on Form S-8)

Each of the undersigned directors of Duluth Holdings Inc., a Wisconsin corporation (the “Company”), designates each of Stephen L. Schlecht, Samuel M. Sato and Michael Murphy, with the power of substitution and resubstitution, as the undersigned’s true and lawful attorney-in-fact for the undersigned and in the undersigned’s name, place and stead to sign for the undersigned and in the undersigned’s name in the capacity as a director of the Company the Registration Statement on Form S-8 relating to the Inducement Restricted Stock Award Agreement to be entered into by and between the Company and Heena Agrawal, and to file the same, with all exhibits thereto, other documents in connection therewith, and any amendments to any of the foregoing, with the Securities and Exchange Commission and any other regulatory authority, granting unto said attorney-in-fact and agent full power and authority to do and perform each and every act and thing requisite and necessary to be done in and about the premises, as fully and to all intents and purposes as the undersigned might or could do in person, hereby ratifying and confirming all that said attorney-in-fact and agent, or the undersigned’s substitute, may lawfully do or cause to be done by virtue hereof.

IN WITNESS WHEREOF, the undersigned have each executed this Power of Attorney, in one or more counterparts, as of this 24th day of January, 2024.

Exhibit 107

Calculation of Filing Fee Table

Form S-8

(Form Type)

Duluth Holdings Inc.

(Exact Name of Registrant as Specified in its Charter)

Table 1. Newly Registered Securities