Solid Black Men&
Man wearing Solid Black Men&
Royal Heather Men&
Navy Heather Men&
Gunmetal Heather Men&
Mint Men&

Chess Not Checkers | Men's Hoodie

Regular price$59.00
Shipping calculated at checkout.

Midweight = "fitted" with minimal stretch. Consider Sizing up one size especially if 2XL or 3XL size.
Heavyweight = very true to size.
See Size Chart (located above sizes) for additional details on both styles.
  • In stock, ready to ship
  • Inventory on the way
FREE SHIPPING on all orders over $99.
Material is a Poly / Airlume combed and ringspun cotton blend

Introducing our "Chess Not Checkers" apparel – a powerful reminder that in the game of business, strategic thinking reigns supreme. Just like a grandmaster on the chessboard, successful entrepreneurs and professionals know that every move counts, and they're always thinking several steps ahead.

Crafted with precision and designed for those who strive for excellence, this apparel is more than just clothing; it's a symbol of your commitment to playing the long game in the world of business. The chessboard graphic on the front represents the intricate decisions and calculated risks that define your journey. It's a visual cue to remind you and others that in business, we don't settle for checkers – we play chess.

Our "Chess Not Checkers" apparel is made from premium materials, ensuring both comfort and durability. Whether you're wearing it to the office, a meeting, or simply as a statement piece, it serves as a conversation starter, sparking discussions about strategy, ambition, and the mindset required to succeed.

Embrace the mindset of a strategist and let this apparel inspire you to think several moves ahead, adapt to changes, and approach challenges with confidence. Remember, in the world of business, it's not about quick wins but about crafting a winning strategy that leads you to long-term success.

Elevate your wardrobe and your mindset with "Chess Not Checkers" apparel – a reminder that in business, the strategic thinker is the one who conquers the board and achieves greatness. Make your move today and seize your destiny in style!

  • 80% pre-shrunk cotton, 20% polyester
  • Fabric weight: 8.5 oz/yd² 
  • Air-jet spun yarn with a soft feel and reduced pilling
  • Double-lined hood with matching drawcord
  • Jersey-lined hood
  • Quarter-turned body to avoid crease down the middle
  • 1 × 1 athletic rib-knit cuffs and waistband with spandex
  • Front pouch pocket
  • Double-needle stitched collar, shoulders, armholes, cuffs, and hem


Size guide - Full size chart click here


Midweight - Provides a more snug/form fitted style. Comfortable fit without being too tight or too loose -  and offer minimal stretch. If you are in-between sizes or prefer a roomier fit, we recommend sizing up. 
Weight = 8.5 oz
Heavyweight - Roomier fit. These are a heavier material, looser fit, giving you room to move around freely while staying warm with stretch. Our heavyweight style is very true to fit. Order your normal hoodie size in this style.
Weight = 10 oz.
All men's hoodies are a Poly/Cotton comfortable blend. Super soft on the inside, and durable for a long-lasting piece.
Like all clothing with any cotton or poly, depending on how you launder it, it may shrink a little. Please keep this in mind when ordering.
To avoid shrinkage, do not wash in hot or very warm water. Best practices are to use "colors" setting on washing machine and hang dry.

All of our apparel is shipped from right here in the United States.

All orders will be shipped as quickly as possible. 

Orders are usually processed within 3 business days. 

All orders, once processed, will typically ship the following business day. 

We cannot control shipping times, depending on the shipping option chosen, items should arrive within 3 to 9 days from the day it was shipped. 

As always, contact us any time with questions or if we can help in any way.

Stay Relentless

Easy NO-HASSLE Returns and Exchanges! Returns and Exchanges

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Text block

Customer Reviews

Based on 1 review
Ralph Parrinello
In the hoodie game RR It’s clearly saying checkmate!

I have written quite a few reviews about these hoodies. I’ve purchased from relentless rebel last week. After looking into the company, I valued what they were about the quality their customers and their brand. As a business owner, I can understand that and standing behind your Product is key. And I have to give credit with credit is due to folks over at RNR are putting it down with their Custom clothing.
They got me sold.
Hoodies that fit me to a T But more like a hoodie, I could tell it was definitely built different as it was inscribed on the front. & they just Happen To have a hoodie with my most Favorite phrase..
It’s chess not checkers!

You May Also Like

Best Selling