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TAILORED BRANDS, INC. 2024 EQUITY INCENTIVE PLAN

Restricted Stock Unit Award Notice – For Name

Tailored Brands, Inc., a Delaware corporation (the “Company”), has granted to you a Restricted Stock Unit Award pursuant to the terms and conditions of the Tailored Brands, Inc. 2024 Equity Incentive Plan (as may be amended or restated from time to time) (the “Plan”) and the Restricted Stock Unit Award Agreement, attached hereto (the “Agreement”). Capitalized terms not defined in this notice (the “Notice”) shall have the meanings specified in the Plan or the Agreement, as applicable. The grant of the Award hereunder is discretionary, and this grant is not a promise or commitment to grant additional Awards at any later date.

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EX-10.11·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

December 1, 2025

Re: Promotion to EVP, Chief Operating Officer

Dear Karla,

Congratulations on your promotion to EVP, Chief Operating Officer.

You are an integral part of the success and future of Tailored Brands, and I am excited about working with you in this new capacity.

As discussed, you will be receiving a promotional increase to your compensation with an effective date of December 1, 2025. Details are in the table below.

Current New % Increase
Base Salary $ 540,000 $ 700,000 29.6 %
AIP Target 75 % 75 %

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EX-10.19·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

January 31, 2024

Peter Sachse

[***]

Re: Offer of Employment

Dear Peter,

The purpose of this letter is to confirm the conditions of your new position as sole Chief Executive Officer.

Effective February 1, 2024:

● You will be hired by Tailored Shared Services, Inc.
● Your pay rate will be $1,000,000 per year.
● Your Annual Incentive Plan (AIP) target is 100% of your base salary.

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EX-10.21·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

January 22, 2025

Whit Alexander
[***]

Re: Offer of Employment

Dear Whit,

On behalf of Tailored Shared Services, LLC (“we “us,” or “the Company”), I am pleased to offer you the position of Executive Vice President and Chief Customer Officer, reporting to me. We are excited to have you join us, and this letter will outline the basic terms and conditions of the position offered.

Your planned start date will be March 3, 2025 (or sooner if possible), at the pay rate of $540,000 per year.

You are eligible to participate in the Company’s Annual Incentive Plan (AIP) with a target of 75% of your base salary. For Fiscal 2025, you will be eligible for 100% of the AIP target with no proration, and otherwise subject to payout per the Company AIP program and business performance. The AIR if earned, is generally paid in April of the following fiscal year. You must be employed by the Company as of the date the bonus is paid to earn any portion of the bonus. The bonus amount will be subject to taxes and withholdings.

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EX-10.17·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

Tailored Brands, Inc. 2025 Director Equity Plan

Article 1
Purpose And Effective Date

** **

**A. **Purpose. The purpose of this Tailored Brands, Inc. 2025 Director Equity Plan is to promote the long-term financial success of the Company, increasing stockholder value by enabling the Company and its related entities to attract and retain the services of those directors who can contribute most effectively to the successful conduct of the Company’s business. These objectives are accomplished by making long-term incentive awards under the Plan that will offer Participants an opportunity to have a greater proprietary interest in, and closer identity with, the Company and its Affiliates and their financial success.

** **

**B. **Effective Date. The Plan shall become effective upon adoption by the Board.

Article 2
Definitions

** **

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EX-10.12·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

TAILORED BRANDS, INC. AMENDED AND RESTATED 2021 EQUITY INCENTIVE PLAN

Restricted Stock Unit Award Notice – For Name

Tailored Brands, Inc., a Delaware corporation (the “Company”), has granted to you a Restricted Stock Unit Award pursuant to the terms and conditions of the Tailored Brands, Inc. Amended and Restated 2021 Equity Incentive Plan (as may be amended or restated from time to time) (the “Plan”) and the Restricted Stock Unit Award Agreement, attached hereto (the “Agreement”). Capitalized terms not defined in this notice (the “Notice”) shall have the meanings specified in the Plan or the Agreement, as applicable. The grant of the Award hereunder is discretionary, and this grant is not a promise or commitment to grant additional Awards at any later date.

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EX-10.7·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

FORM OF DIRECTOR NOMINATION AGREEMENT

Tailored Brands, Inc. / DE

FORM OF
DIRECTOR NOMINATION AGREEMENT

This Director Nomination Agreement (this “Agreement”), dated as of [●], 2026, is entered into by and between Tailored Brands, Inc., a Delaware corporation (the “Company”), and Silver Point Capital, L.P., a Delaware limited partnership (“Silver Point”). The Agreement shall be effective from the Effective Date (as defined herein).

WHEREAS, the Company intends to consummate an initial public offering (“IPO”) of shares of its common stock, par value $0.001 per share (the “Common Stock”); and

WHEREAS, in connection with such events, the parties hereto desire to provide for certain governance rights and other matters with respect to the Company upon the consummation of the IPO (the “Effective Date”).

NOW, THEREFORE, in consideration of and reliance upon the mutual covenants and agreements contained herein, and for other good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, the parties hereto agree as follows:

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EX-10.4·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

Execution Version

9.000% SENIOR SECURED NOTES DUE 2031

INDENTURE

Dated as of January 28, 2026

Among

THE MEN’S WEARHOUSE, LLC

as Issuer,

the Guarantors party hereto from time to time

and

U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION

as Trustee and

Notes Collateral Agent

TABLE OF CONTENTS

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EX-10.3·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

TAILORED BRANDS, INC. 2024 EQUITY INCENTIVE PLAN

Restricted Stock Unit Award Notice – For Name

Tailored Brands, Inc., a Delaware corporation (the “Company”), has granted to you a Restricted Stock Unit Award pursuant to the terms and conditions of the Tailored Brands, Inc. 2024 Equity Incentive Plan (as may be amended or restated from time to time) (the “Plan”) and the Restricted Stock Unit Award Agreement, attached hereto (the “Agreement”). Capitalized terms not defined in this notice (the “Notice”) shall have the meanings specified in the Plan or the Agreement, as applicable. The grant of the Award hereunder is discretionary, and this grant is not a promise or commitment to grant additional Awards at any later date.

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EX-10.10·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

April 21, 2021

Karla Gray
[***]

Re: Offer of Employment

Dear Karla,

On behalf of Tailored Shared Services, LLC (“we,” “us,” or “the Company”), I am pleased to offer you the position of Executive Vice President of Stores. We are excited to have you join us, and this letter will outline the basic terms and conditions of the position offered.

Your start date will be May 3, 2021 (or a date mutually agreed upon), at the pay rate of $415,000 per year. Your direct manager will be Peter Sachse, Co-Chief Executive Officer.

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EX-10.18·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

Dear Jamie,

As EVP, Chief Supply Chain Officer of Tailored Brands, your leadership in the coming year will be critical to us achieving both our short term financial objectives as well as making progress against longer term strategic positioning and objectives. The purpose of this letter is to outline your target compensation for 2019 and illustrate for you how the achievement of these short and long term objectives will directly impact your actual compensation. Your 2019 Total Direct Compensation (at target) of $1,233,750 consists of three components:

1. FY19 Base Salary: $475,000
2. FY19 Bonus Target: $308,750

Your bonus consists of 3 parts:

● Company EBIT Target (60%) — $185,250

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EX-10.20·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET

TAILORED BRANDS, INC. 2024 EQUITY INCENTIVE PLAN

I INTRODUCTION

1.1 Purposes. The purposes of the Tailored Brands, Inc. 2024 Equity Incentive Plan (this “Plan”) are (i) to align the interests of the Company’s stockholders and the recipients of awards under this Plan by increasing the proprietary interest of such recipients in the Company’s growth and success, (ii) to advance the interests of the Company by attracting and retaining highly qualified officers and employees and (iii) to motivate such persons to act in the long-term best interests of the Company and its stockholders.

1.2 Certain Definitions.

“Agreement” shall mean the written or electronic agreement evidencing an award hereunder between the Company and the recipient of such award.

“Board” shall mean the Board of Directors of the Company.

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EX-10.9·S-1·CIK 2045151·ACC 0001213900-26-077111·Filed Jul 10, 2026, 15:38 ET