Gambler Style Hats

…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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  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…

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…conservative look. The braided leather hat band and tassel accent add just a touch of style.     Approx. 3 7/8" Gambler Crown 2 1/2" Brim   Made of: 100% Genuine Leather   Packable/Crushable Build Distressed, Matte Finish Braided Leather Hat Band Tassel Accent Underwelt…

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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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  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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…and narrower fit. Updated sizing for the style is listed below or you may call us at 1-888-847-4287 for help with sizing.  S = 6 7/8 M = 7 1/8 L = 7 3/8 XL = 7 5/8   Made in the USA   The Stetson Kelso Crushable Wool Felt Gambler Western Hat features a gambler-style crown crafted…

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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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…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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…  Since 1929, Eddy Bros has been making quality hats with style and class and the same goes for the Reed Toyo Straw Gambler Hat. This gambler has a stiff build with the classic telescope crown and dramatically flared brim. The hat band is made of leather with metal concho accents while…

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…Looking for a gambler at an affordable price...the Crossfire Wool Felt Gambler Hat has been thoughtfully designed by Jaxon Hats to bring you a low-cost option of this popular hat shape. Packable/crushable and made of 100% wool, the Crossfire is adorned with a faux leather hat band. Silver metallic…

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…USA   The Kalama Panama Straw Gambler Hat by Tommy Bahama features the classic telescope crown. This wide brim Panama hat will keep you protected from the sun while out in style. The elasticized COOLMAX® sweatband is so comfortable, you'll wear this hat all day long!   Approx. 3…

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  Jaxon Hats' newest leather hat, the Crusher Leather Outback Hat, is made of 100% genuine leather with a gorgeous matte finish. This hat is all about being sleek, from the braided leather hat band to the semi-circle leather sweatband. If your looking for a hat that's a little bit different…

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