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  Conner's Hemp Gambler Hat is a great piece for those that prefer a more structured item. The hemp material keeps the weight of the hat light but continues to give protection from the elements.   Approx. 4" Crown 2 3/4" Brim   Made of: 100% Hemp  …



…matter, that's why we know you'll love the Panama Straw Gambler Hat from Scala! This phenomenal hat is handwoven in Ecuador, then blocked and finished in the United States, resulting in one beautiful, well-made gambler. Additionally, the grosgrain ribbon hat band and Scala metal side pin…


Kenny 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…


Kenny K

  Keep the sun off and look your best on the golf course with the stylish Back Nine Straw Gambler Hat by Kenny K! Made of lightweight straw in a classic gambler hat design, the Back Nine Gambler features a telescope crown and wide, upturned brim. A 3-pleat, tropic printed hat band encircles…


Jaxon Hats

  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…



  The Conner Deluxe Toyo Straw Gambler 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…


Tommy Bahama

UPF 50+   Enhance your wardrobe with the Andros Toyo Straw Gambler Hat from Tommy Bahama! This gambler is so fashionable, thanks in part to its chic 3-pleat cotton hat band wrapping around the crown, adorned with the removable marlin side pin. Additionally, the unlined interior is…


Jaxon Hats

…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 you cool on those hot summer…


Charlie 1 Horse

…Wool Felt Gambler Hat from Charlie 1 Horse is a high-quality hat. Made in America, this hat is pure, durable, comfortable wool, with a soft satin interior lining that just cannot be ignored. Additionally, the leather hat band matches the leather sweatband, making for one beautiful, quality gambler.

Compare: $174.37
SAVE $17 (10%)


  Made in the USA Introducing the Joker LiteFelt® Wool Gambler 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®…

Compare: $97.65
SAVE $9 (10%)


…enjoys relaxing bayside or taking part in outdoor activities. Made of twisted seagrass, the open weave allows for maximum ventilation of this gambler hat. A fashionable and attractive leopard scarf wraps around the crown, ending in a bow.   Approx. 4" Crown 3 1/4" Brim  …

Compare: $52.31
SAVE $9 (18%)

Jaxon Hats

…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.    Constructed of stiff seagrass, the gambler features a handsome 3-pleat cotton headband and an elasticized…