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Shop men’s gambler hats made of top-quality wool felt, seagrass, and straw to make sure you’re ready for anything. It’s time to go on an adventure you’ll never forget.


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  1. Renegade by Bailey® Chancy 2X - Black/6 3/4
    Renegade by Bailey® Chancy 2X
    Starting at $120.00
  2. Eddy Bros.® Gambler - Black/M
    Eddy Bros.® Gambler
    Starting at $59.00
  3. Renegade by Bailey® Joker Western Hat - Black/L
    Renegade by Bailey® Joker Western Hat
    Starting at $84.00
  4. Eddy Bros.® Black Hills Gambler - Black/XL
    Eddy Bros.® Black Hills Gambler
    Starting at $53.00
  5. Renegade Renegade by Bailey® Ellsworth Western Hat - Mist
    Renegade by Bailey® Ellsworth Gambler
    Starting at $105.00
  6. Joseph Weave Gambler - Natural/M
    Joseph Weave Gambler
    Starting at $55.00
  7. Melton Gambler - Natural/S
    Melton Gambler
    Starting at $125.00

7 Items

per page
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Gambler Cowboy Hat

At Hats.com, it’s our mission to provide you with a premier collection of men’s hats to enhance your style. If you’re looking for something that evokes the wild freedom of the untamed West, a gambler cowboy hat could be the perfect choice for you. With their distinct oval-shaped crown and brim, they’re very similar to a regular cowboy hat ㅡ but often with extra embellishments and details.

Striking Statement Pieces

A gambler cowboy hat offers you a distinctive fashion choice. It imbues you with a confidence and boldness that defines your style. These hats aren’t for those who play it safe!

We carry gamblers that are carefully crafted and designed for the summer, spring, and winter seasons so you can look your best no matter the time or place. With leading brands like Country Gentlemen, Bailey of Hollywood, and Renegade, you can find a high-quality statement piece that fits with your aesthetic.

Unleash Your Inner Renegade

The gambler is a rugged and stylish hat that only gets more sophisticated with passing years. With this timeless style, you’ll personify the same risk-taking, forward-thinking essence that the hat’s name suggests.

Check out our selection of high-quality men’s gambler hats to discover unique styles and specialty designs.

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