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  1. Main Image
    Ace of Spades Gambler Hat - Exclusive
    Starting at $39.99
  2. Eddy Bros. Gambler
    Eddy Bros. Gambler
    Starting at $59.00
  3. Renegade by Bailey® Joker Western Hat
    Renegade by Bailey® Joker Western Hat
    Starting at $84.00
  4. Eddy Bros. Black Hills Gambler
    Eddy Bros. Black Hills Gambler
    Starting at $53.00
  5. Renegade by Bailey® Ellsworth Gambler
    Renegade by Bailey® Ellsworth Gambler
    Starting at $105.00
  6. Wenrich Bolero
    Wenrich Bolero
    Starting at $300.00
  7. Main Image
    Joseph Weave Gambler
    Starting at $48.00
  8. Rockett Raindura® Gambler
    Rockett Raindura® Gambler
    Starting at $110.00

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At, it’s our mission to carry this season’s premier online collection of men’s hats that boost your style, which is why we supply the gambler hat. Gamblers evoke the outback and the wild west with their distinct oval-shaped crown and brim. We make our gamblers from top-quality wool felt, and offer other fine materials so you stay comfortable while setting yourself apart from the crowd. Go right ahead, find a gambler hat that suits your style and have yourself an adventure you’ll never forget. 

Top-Quality Gambler Hats

A well-made men’s gambler hat is the premier choice for men whose confidence and boldness defines their style. These hats aren’t for those who like to play it safe with their fashion, as they effortlessly draw admiring glances from passersby. Our premium selection offers you the opportunity to have a gambler hat to match your style and personality. With leading brands like Country Gentlemen, Bailey of Hollywood, and Renegade, there’s nothing stopping you from taking charge of your style with a well-constructed, respected hat.

Unleash Your Inner Renegade  

The gambler is a rugged and stylish hat that only takes on a more sophisticated look with the passing years. With this unfading style, you’ll personify the same risk-taking, forward-thinking essence that the hat’s name suggests. 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. Shop our selection of high-quality gambler hats and get ready to seize the day.