Exhibit 10.1

AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

This AMENDMENT NUMBER ONE TO AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT (this “Amendment”), dated as of April 12, 2023, is entered into by and among GUESS ?, INC., a Delaware corporation (“Parent”), GUESS? RETAIL, INC., a Delaware corporation (“Retail”), GUESS.COM, INC., a Delaware corporation (“Com”; and together with Parent, and Retail, each a “U.S. Borrower” and collectively, the “U.S. Borrowers”), GUESS? CANADA CORPORATION, a company amalgamated under the laws of the province of Nova Scotia, Canada (“Canadian Borrower”; and together with U.S. Borrowers, each a “Borrower” and collectively, the “Borrowers”), Parent and certain Subsidiaries of Parent party to the Loan Agreement as guarantor (each, a “Guarantor” and collectively, the “Guarantors”), the financial institutions party thereto from time to time as lenders (the “Lenders”), and BANK OF AMERICA, N.A., a national banking association, as agent for the Lenders and solely with respect to the loan servicing requirements of the Canadian Borrowers, Bank of America-Canada Branch (the “Agent”).

RECITALS

A.        WHEREAS, Borrowers, Guarantors, Agent, and Lenders are parties to that certain Amended and Restated Loan, Guaranty and Security Agreement, dated as of December 20, 2022 (the “Existing Loan Agreement”, and as such agreement may be amended, restated amended and restated, supplemented, extended or otherwise modified in writing from time to time, including by this Amendment, the “Loan Agreement”); and

B.        WHEREAS, Borrowers have requested and Agent and Lenders agreed to amend the Loan Agreement in certain respects, pursuant to the terms and subject to the conditions, as set forth in this Amendment.

AGREEMENT

NOW, THEREFORE, in consideration of the foregoing and the mutual covenants herein contained, and for good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereby agree as follows:

ARTICLE I

DEFINITIONS; RECITALS

Section 1.01. Definitions. Initially capitalized terms used but not defined in this Amendment have the respective meanings set forth in the Loan Agreement, as amended hereby.

Section 1.02. Recitals. The Recitals above are incorporated herein as though set forth in full and the Obligors stipulate to the accuracy of each of the Recitals.

ARTICLE II

AMENDMENTS TO LOAN AGREEMENT

Section 2.01. New Definitions. The following new definitions are hereby added to Section 1.1 of the Existing Loan Agreement in alphabetical order to read in their entirety as follows:

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First A&R Amendment: that certain Amendment Number One to Amended and Restated Loan, Guaranty and Security Agreement dated as of the First A&R Amendment Effective Date by and among Borrowers, Guarantors, Agent and Lenders.

First A&R Amendment Effective Date: April 12, 2023.

Permitted Convertible Note Debt (2019): the Debt and other obligations incurred by Parent on or about April 26, 2019 pursuant to the Permitted Convertible Note Documents (2019) which include (i) the Permitted Convertible Notes (2019) and (ii) any Debt and other obligations under the Hedging Agreements and other agreements, in each case, entered into in connection with the Permitted Convertible Note Debt (2019) and Permitted Convertible Note Documents (2019), and any renewals, extensions or refinancings thereof, as long as each Refinancing Condition is satisfied.

Permitted Convertible Note Documents (2019): that certain indenture, dated as of April 26, 2019, between Parent and U.S. Bank National Association, as trustee providing for the issuance of the Permitted Convertible Notes, together with the Permitted Convertible Notes (2019), Hedging Agreements in connection with the Permitted Convertible Note Debt (2019) and other documents executed or delivered by Parent in connection therewith, in each case, as amended, replaced, supplemented, extended, refinanced or otherwise modified from time to time so long as, in the case of any renewal, extension or refinancing, each Refinancing Condition is satisfied.

Permitted Convertible Notes (2019): convertible notes in the original aggregate principal amount of $300,000,000 issued on or about April 26, 2019 pursuant to the Permitted Convertible Note Documents (2019), in each case, as amended, replaced, supplemented, extended, refinanced or otherwise modified from time to time so long as, in the case of any renewal, extension or refinancing, each Refinancing Condition is satisfied.

Permitted Share Repurchases (2019): the purchase, redemption or other acquisition or retirement of common Equity Interests of the Parent with the proceeds of the issuance of the Permitted Convertible Note Debt (2019).

Permitted Convertible Note Debt (2023): the Debt and other obligations incurred by Parent around the First A&R Amendment Effective Date pursuant to the Permitted Convertible Note Documents (2023) which include (i) the Permitted Convertible Notes (2023) and (ii) any Debt and other obligations under the Hedging Agreements and other agreements, in each case, entered into in connection with the Permitted Convertible Note Debt (2023) and Permitted Convertible Note Documents (2023), and any renewals, extensions or refinancings thereof, as long as each Refinancing Condition is satisfied.

Permitted Convertible Note Documents (2023): that certain indenture, to be dated around the First A&R Amendment Effective Date, between Parent and U.S. Bank Trust Company National Association, as trustee providing for the issuance of the Permitted Convertible Notes (2023), together with the Permitted Convertible Notes (2023), Hedging Agreements in connection with the Permitted Convertible Note Debt (2023) and other documents executed or delivered by Parent in connection therewith, in each case, as amended, replaced, supplemented, extended, refinanced or otherwise modified from time to time so long as, in the case of any renewal, extension or refinancing, each Refinancing Condition is satisfied.

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Permitted Convertible Notes (2023): convertible notes in an aggregate principal amount up to but not exceeding $350,000,000 issued around the First A&R Amendment Effective Date pursuant to the Permitted Convertible Note Documents (2023), in each case, as amended, replaced, supplemented, extended, refinanced or otherwise modified from time to time so long as, in the case of any renewal, extension or refinancing, each Refinancing Condition is satisfied.

Permitted Share Repurchases (2023): the purchase, redemption or other acquisition or retirement of common Equity Interests of the Parent with the proceeds of the issuance of the Permitted Convertible Note Debt (2023), provided that immediately before and after such repurchases (i) no Default or Event of Default exists and (ii) Availability is in an amount equal to or greater than 17.5% of the aggregate Borrowing Base (calculated based on the most recently delivered Borrowing Base Report) on average during the thirty (30) days immediately before giving effect thereto and immediately after giving pro forma effect thereto and Parent shall have delivered a certificate to Agent certifying the satisfaction of clauses (i) and (ii) above.

Section 2.02. Amendment to the Definition “Permitted Asset Disposition” in Section 1.1 of the Existing Loan Agreement. The definition “Permitted Asset Disposition” in Section 1.1. of the Existing Loan Agreement is hereby amended by amending and restating clause (r) thereof in its entirety to read as follows:

(r) the unwinding of any Hedging Agreements in connection with the Permitted Convertible Note Debt including those entered into by Parent on or about the Second Amendment Effective Date or around the First A&R Amendment Effective Date and any Hedging Agreements entered into by Parent in connection with any permitted refinancing of any Permitted Convertible Note Debt, in each case, in accordance with their terms in connection with the payment, repurchase or conversion of the Permitted Convertible Notes;

Section 2.03. Amendment to the Definition “Permitted Convertible Note Debt” in Section 1.1 of the Existing Loan Agreement. The definition “Permitted Convertible Note Debt” in Section 1.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

Permitted Convertible Note Debt: the (a) Permitted Convertible Note Debt (2019), and (b) Permitted Convertible Note Debt (2023).

Section 2.04. Amendment to the Definition “Permitted Convertible Note Documents” in Section 1.1 of the Existing Loan Agreement. The definition “Permitted Convertible Note Documents” in Section 1.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

Permitted Convertible Note Documents: the (a) Permitted Convertible Note Documents (2019) and (b) Permitted Convertible Note Documents (2023).

Section 2.05. Amendment to the Definition “Permitted Convertible Notes” in Section 1.1 of the Existing Loan Agreement. The definition “Permitted Convertible Notes” in Section 1.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

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Permitted Convertible Notes: the (a) Permitted Convertible Notes (2019) and (b) Permitted Convertible Notes (2023).

Section 2.06. Amendment to the Definition “Permitted Share Repurchases” in Section 1.1 of the Existing Loan Agreement. The definition “Permitted Share Repurchases” in Section 1.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

Permitted Share Repurchases: the (a) Permitted Share Repurchases (2019) and (b) Permitted Share Repurchases (2023).

Section 2.07. Amendment to the Definition “Revolver Termination Date” in Section 1.1 of the Existing Loan Agreement. The definition “Revolver Termination Date” in Section 1.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

Revolver Termination Date: the earlier of (a) December 20, 2027 and (b) the date which is 60 days prior to the stated maturity date of the Permitted Convertible Notes (2019) unless (i) prior to such 60 day period such convertible notes have been refinanced in full or converted into the Equity Interests of Parent in full, (ii) no later than 5 Business Days prior to such 60 day period, the Obligors demonstrate to the Lenders’ satisfaction (determined in each Lender’s sole and absolute discretion) that such convertible notes will be refinanced in full or converted to the Equity Interests of Parent in full prior to stated maturity date thereof and no obligations will be outstanding thereunder on the stated maturity date thereof, or (iii) the Payment Conditions, calculated on a pro forma basis after giving effect to the full repayment of such convertible notes, are satisfied on each day during such 60 day period, and immediately after giving effect thereto (it being understood that if the Payment Conditions fail to be satisfied during such 60 day period and neither clause (i) or (ii) is applicable, the Revolver Termination Date shall occur), and Parent shall have delivered to Agent certificates, in form and substance reasonably satisfactory to Agent, certifying and demonstrating that the Payment Conditions, calculated on a pro forma basis after giving effect to the full repayment of such convertible notes, are met on (x) the 61^st day prior to the stated maturity date of the Permitted Convertible Notes (2019), (y) any other date during such 60 day period on which Parent is required to deliver a Borrowing Base Report to Agent, and (z) any other date on which Parent requests a Revolving Loan or the issuance of a Letter of Credit. For the avoidance of doubt, a certificate shall be required to be delivered upon the occurrence of each of the dates or events set forth in subclauses (x), (y) and (z) above.

Section 2.08. Amendment to Clause (u) in Section 10.2.1 of the Existing Loan Agreement. Clause (u) in Section 10.2.1 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

(u) other unsecured Debt (i) incurred prior to the Closing Date in the aggregate principal amount not exceeding $500,000,000 as set forth on Schedule 10.2.1(u), (ii) incurred on or after the Closing Date in an aggregate principal amount at any one time outstanding not to exceed an amount equal to $500,000,000 minus, if applicable, any outstanding principal amount of Permitted Convertible Notes in excess of $440,000,000 (it being understood that Permitted Convertible Notes in the outstanding principal amount of up to $440,000,000 shall not reduce capacity under this clause (u)(ii)), (iii) pursuant to loan agreements, indentures or other documentation having covenants and other terms with

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respect to the Obligors that are no more restrictive in any material respect than those in this Agreement, and (iv) with a maturity date after the Revolver Termination Date; and

Section 2.09. Amendment to Clause (e) in Section 10.2.4 of the Existing Loan Agreement. Clause (e) in Section 10.2.4 of the Existing Loan Agreement is hereby amended and restated in its entirety to read as follows:

(e) Permitted Share Repurchases and, for the avoidance of doubt, (A) payments on or about the Second Amendment Effective Date pursuant to the Hedging Agreements entered into in connection with the Permitted Convertible Note Debt (2019), (B) payments around the First A&R Amendment Effective Date pursuant to the Hedging Agreements entered into in connection with the Permitted Convertible Note Debt (2023), (C) payments pursuant to any Hedging Agreements entered into by Parent in connection with any permitted refinancing of the applicable Permitted Convertible Note Debt, and (D) the settlement of any related Hedging Agreement entered into in connection with the applicable Permitted Convertible Note Debt under which Parent may be obligated to deliver common Equity Interests of the Parent, including (i) by delivery of common Equity Interests of the Parent or (ii) by (x) payment of a net amount in cash in respect of any early termination or maturity of any Hedging Agreement entered into in connection with the applicable Permitted Convertible Note Debt or (y) delivery of common Equity Interests of the Parent or payment of a net amount in cash upon an early termination or maturity of any such Hedging Agreement;

For the avoidance of doubt, Section 10.2.4 shall otherwise remain in full force and effect.

Section 2.09. Amendment to Clause (b) in Section 10.2.8 of the Existing Loan Agreement. Clause (b) in Section 10.2.8 of the Existing Loan Agreement is hereby amended by (x) deleting the word “and” appearing prior to clause (vii), (y) adding a new word “and” at the end of clause (vii) and (z) adding a new clause (viii) at the end thereof as follows:

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(viii) exchanges of the Permitted Convertible Notes (2019) for the Permitted Convertible Notes (2023) and repurchases or repayments of the Permitted Convertible Notes (2019) with the proceeds of the Permitted Convertible Notes (2023), provided that immediately before and after such exchanges, repurchases or repayments (i) no Default or Event of Default exists and (ii) Availability is in an amount equal to or greater than 17.5% of the aggregate Borrowing Base (calculated based on the most recently delivered Borrowing Base Report) on average during the thirty (30) days immediately before giving effect thereto and immediately after giving pro forma effect thereto and Parent shall have delivered a certificate to Agent certifying the satisfaction of clauses (i) and (ii) above;

ARTICLE III

CONDITIONS TO EFFECTIVENESS; MISCELLANEOUS

Section 3.01. Conditions to Effectiveness. The parties hereto agree that the amendments set forth herein shall not be effective until the satisfaction of each of the following conditions precedent:

(a) Executed Amendment. The Agent shall have received a fully executed copy of this Amendment signed by the Borrowers, Guarantors, Agent and Lenders.

Section 3.02. Miscellaneous.

(a) Survival of Representations and Warranties. All representations and warranties made in the Loan Agreement or any other document or documents relating thereto, including, without limitation, any Loan Document furnished in connection with this Amendment, shall survive the execution and delivery of this Amendment and the other Loan Documents, and no investigation by Agent or the Lenders shall affect the representations and warranties or the right of the Lenders or Agent to rely thereon.

(b) Reference to Loan Agreement. The Loan Agreement, each of the Loan Documents, and any and all other agreements, documents or instruments now or hereafter executed and delivered pursuant to the terms hereof, or pursuant to the terms of the Loan Agreement as amended hereby, are hereby amended so that any reference therein to the Loan Agreement shall mean a reference to the Loan Agreement as amended hereby.

(c) Loan Agreement Remains in Effect. The Loan Agreement and the Loan Documents, as amended hereby, remain in full force and effect and each Borrower and each Guarantor ratifies and confirms its agreements and covenants contained therein. Each Borrower and each Guarantor hereby confirms that to the best of its knowledge no Event of Default or Default exists.

(d) Severability. Any provision of this Amendment held by a court of competent jurisdiction to be invalid or unenforceable shall not impair or invalidate the remainder of this Amendment and the effect thereof shall be confined to the provision so held to be invalid or unenforceable.

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(e) Counterparts; Facsimile. This Amendment may be executed in one or more counterparts, each of which when so executed shall be deemed to be an original, but all of which when taken together shall constitute one and the same instrument. Delivery of an executed counterpart to this Amendment by facsimile or other electronic means (including in “.pdf” or “.tif” format) shall be effective as an original.

(f) Headings. The headings, captions and arrangements used in this Amendment are for convenience only and shall not affect the interpretation of this Amendment.

(g) NO ORAL AGREEMENTS. THIS AMENDMENT, TOGETHER WITH THE OTHER LOAN DOCUMENTS AS WRITTEN, REPRESENTS THE FINAL AGREEMENT BETWEEN LENDERS, AGENT, BORROWERS AND GUARANTORS AND MAY NOT BE CONTRADICTED BY EVIDENCE OF PRIOR, CONTEMPORANEOUS OR SUBSEQUENT ORAL AGREEMENTS OF THE PARTIES. THERE ARE NO UNWRITTEN ORAL AGREEMENTS BETWEEN AGENT, LENDERS, BORROWERS AND GUARANTORS.

(h) GOVERNING LAW. THIS AMENDMENT SHALL BE GOVERNED BY THE LAWS OF THE STATE OF NEW YORK, WITHOUT GIVING EFFECT TO ANY CONFLICT OF LAW PRINCIPLES (BUT GIVING EFFECT TO FEDERAL LAWS RELATING TO NATIONAL BANKS); PROVIDED, HOWEVER, THAT IF THE LAWS OF ANY JURISDICTION OTHER THAN NEW YORK SHALL GOVERN IN REGARD TO THE VALIDITY, PERFECTION OR EFFECT OF PERFECTION OF ANY LIEN OR IN REGARD TO PROCEDURAL MATTERS AFFECTING ENFORCEMENT OF ANY LIENS IN COLLATERAL, SUCH LAWS OF SUCH OTHER JURISDICTIONS SHALL CONTINUE TO APPLY TO THAT EXTENT.

[Signature Pages to Follow]

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IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be duly executed by its authorized officers as of the day and year first above written.

AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

(GUESS?)

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AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

(GUESS?)

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AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

(GUESS?)

SIGNATURE PAGE

AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

(GUESS?)

SIGNATURE PAGE

AMENDMENT NUMBER ONE TO

AMENDED AND RESTATED LOAN, GUARANTY AND SECURITY AGREEMENT

(GUESS?)

SIGNATURE PAGE