Gambler Style Hats

The Western Wool Felt Gambler Hat by Eddy Bros features a classic telescope crown gambler style with a western twist. Crafted of 100% wool felt with a soft, packable finish, the Western Gambler is accented with a western-inspired conch faux leather hat band tied at the side. Unlined for better…

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…Western Hat by Renegade. This is a great wool gambler with a stylish studded leather hat band and flared, upturned brim. Made in the USA by expert craftsmen, the Joker features their exclusive wool LiteFelt® finish that makes this style both packable/crushable and water repellent. No stiff hats…

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  The Jaxon Wool Gambler Hat is a dapper and stylish hat with a slight western flair. This hat embodies the same fast talking, risk-taking style that the name suggests. Featuring a telescope crown, this Wool Gambler is ready for adventure!   Approx. 3 3/8" Underwelt Brim 3 5/8"…

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  Made in the USA   The Stetson Kelso Crushable Wool Felt Gambler Western Hat features a gambler-style crown crafted of crushable wool felt. Adorned with a faux leather hat band overlaid with feathers, the Kelso is finished with a Stetson metal side pin, slightly flared brim and…

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…  Made of twisted genuine Panama straw, Pantropic's Twisted Panama Straw Gambler Hat features a loose weave in a classic gambler hat style. Handwoven in Ecuador then blocked and finished in the USA, this style represents hours of artisanal work and specialized craftsmanship. Renowned for…

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  Made in the USA   A classic gambler style with a western edge, the Rockett Raindura Straw Gambler Hat by Bailey features their exclusive new Raindura Finish which helps the hat maintain its shape even after getting wet. Pliable and completely packable, Rockett has a crease down its…

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…Hat offers an elegant and classic style in lightweight and breathable Toyo straw. Featuring a black grosgrain ribbon hatband and 3-inch, slightly upturned brim, this timeless hat is finished with an elastic cotton sweatband. Perfect for spring and summer - the Conner Deluxe Toyo Straw Gambler Hat…

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…original hat size.   Handwoven in Ecuador; Blocked & Finished in the USA   Whether you're headed to the beach or just shading yourself in style, the Jaxon Gambler Cuenca Grade 3 Panama Hat is the perfect choice. Lightweight with consistent weaving, this Panama Hat will keep…

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  Stay in style while relaxing in the Planter Tassel Trim Wool Gambler Hat from Scala. The focus of this clean hat is the intriguing hat band, a beautiful combination of stitched colors and extra decoration. Fun and flirty, this hat has it all!   Approx. 3 1/2" Crown 3 5/8" Floppy…

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…K has struck gold with the Two Tone Toyo Straw Gambler Hat! This fashionable gambler features a zigzag striped weave that's so in style right now, as well as a grosgrain ribbon hat band and bow. Thanks to it's sun-resistant build, this gambler is perfect for any time spent outside this season! …

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  Made in the USA   The Stetson Pin Seeker Hemp Straw Gambler Hat boasts a distinctive and handsome aesthetic not often seen in gambler styles. Crafted of premium hemp braid right here in the USA, the Pin Seeker is an ode to expert craftsmanship and exudes elegance in its simplicity.…

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  Please Note: This style has a shallow fit. This is the intended fit of the hat, please note before purchasing.    As you look out from underneath your Jaxon Pebble Beach Gambler Hat,  you're set for a birdie on the next hole . . . Jack Nicklaus couldn't beat you today.    …

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