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Charlie 1 Horse

…Scars Wool Gambler Hat from Charlie 1 Horse is simply the top of the line! Decked out fully in subtle Charlie 1 Horse decor, this hat features a metal pin on its grosgrain hat band, as well as an authentic Charlie 1 Horse logo branding on its crown. Live the life of luxury with this hat.  …

Compare: $186.00
SAVE $18 (10%)

Eddy Bros

…  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…

Compare: $62.77
SAVE $6 (9%)


…Looking for a Gambler hat with a distinctive look? The new Colonel Shantung Straw Gambler Hat by Stetson is just the thing! Crafted right here in the USA of premium shantung straw, the Colonel Gambler boasts a firm finish, curled wide brim and a classic grosgrain ribbon hat band. The Colonel's…


Eddy Bros

…with a telescope crown and flared brim, the Little Joe Wool Felt Gambler Western Hat by Eddy Bros is not your usual western hat. Floral embossing, metal button accents and triple chain detailing at the front of its faux leather hat band give the Little Joe an edgy feel. Made with a stiff finish, the…

Compare: $46.50
SAVE $4 (10%)


…  Simple, yet classy, the St. Charles Shantung Straw Gambler Hat from Dobbs is stunning. This hat features a grosgrain ribbon hat band with a Dobbs metal side pin, making for a clean design. This American-made hat also has a woven sweatband and unlined interior, allowing for comfort…



…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 are undeniably…



  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…

Compare: $191.81
SAVE $63 (33%)


  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  …



…You can stay laid back with the Explorer Panama Straw Gambler Hat from Bigalli. This panama straw hat features a padded sweatband and unlined interior, which are comfortable and breathable. Additionally, the stitched leather hat band is eye-catching and unique.   Approx. 3 3/4"…


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…

Compare: $58.07
SAVE $5 (9%)


…& Finished in the USA   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…

Compare: $172.05
SAVE $43 (25%)


…ready for something new with the Melton LiteStraw® Seagrass Gambler Hat from Bailey! This unique hat is made with seagrass, a durable and stain-resilient material perfect for any stylish adventurer. No matter your plans, this hat should be your go-to!   Approx. 3 1/2" Telescope…