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  1. Black Hills Gambler
    Black Hills Gambler
    Regular Price $65.00 Starting at $48.75
  2. Chancy 2X
    Chancy 2X
    Regular Price $170.00 Starting at $127.50
  3. Gambler
    Starting at $70.00
  4. Joker Western Hat
    Joker Western Hat
    Starting at $110.00
  5. Wenrich Bolero
    Wenrich Bolero
    Regular Price $300.00 Starting at $225.00
  6. Ellsworth Gambler
    Ellsworth Gambler
    Starting at $140.00
  7. Melton Gambler
    Melton Gambler
    Starting at $145.00
  8. Rockett Raindura® Gambler
    Rockett Raindura® Gambler
    Starting at $130.00
  9. Hats - Mauve
    305S Gambler
    Starting at $115.00

9 Items

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Gambler Cowboy Hat

At, 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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