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    • Small
      Pequeuño
      Size
      6
      3/4
      -
      6
      7/8
      Tamaño
      21
      1/8
      "
      -
      21
      1/2
      "
      54
      cm
      -
      55
      cm
    • Medium
      Medio
      Size
      7
      -
      7
      1/8
      Tamaño
      21
      7/8
      "
      -
      22
      1/4
      "
      56
      cm
      -
      57
      cm
    • large
      Grande
      Size
      7
      1/4
      -
      7
      3/8
      Tamaño
      22
      5/8
      "
      -
      23
      "
      58
      cm
      -
      59
      cm
    • X-Large
      X-Grande
      Size
      7
      1/2
      -
      7
      5/8
      Tamaño
      23
      1/2
      "
      -
      23
      7/8
      "
      60
      cm
      -
      61
      cm
    • XX-Large
      XX-Grande
      Size
      7
      3/4
      -
      7
      7/8
      Tamaño
      24
      1/4
      "
      -
      24
      5/8
      "
      62
      cm
      -
      63
      cm
    • XXX-Large
      XXX-Grande
      Size
        8
       - 
      8 +
      Tamaño
      25
      "
      -
      25
      3/8
      "
      64
      cm
      -
      65
      cm
  • This is a General Hat Sizing Chart: Please read each hat product page for further sizing information.
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Leather Gambler

1 - 21 of 21 Products
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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 from the norm, the Crusher Leather Outback Hat is a perfect fit.   Approx. 3 3/4" Gambler

$78.00
Available Colors:
  • BROWN
  • BLACK

  Made in the USA   Get 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! …

(4)
$125.00
Available Colors:
  • NATURAL

…Felt Gambler Cowboy Hat, part of the Stetson Outdoor Collection. The Black Hawk serves a gambler crown trimmed with silver-tone studs, concho accented black leather band and black leather tails. Best of all the Black Hawk is water resistant and crushable!   Approx. 3 7/8" Gambler Crown…

$109.00
Available Colors:
  • SILVERBELLY

…Felt Gambler Cowboy Hat, part of the Stetson Outdoor Collection. The Black Hawk serves a gambler crown trimmed with silver-tone studs, concho accented black leather band and black leather tails. Best of all the Black Hawk is water resistant and crushable!   Approx. 3 7/8" Gambler Crown…

(54)
$109.00
Available Colors:
  • BLACK

  Made in the USA   The Tattoos and Scars Wool Felt 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…

(2)
$169.00
Available Colors:
  • BLACK

  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…

$52.00
Available Colors:
  • BLACK

…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 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…

(6)
$109.00

  Made in Mexico   Stay cool with the Brentwood Shantung Straw Gambler Hat from Stetson. This high-quality hat is made in Mexico and features a beautiful shantung straw vented crown that maintains a cool, comfortable, breathable fit. Speaking of comfortable and breathable, the cotton…

(3)
$49.95
Available Colors:
  • NATURAL

…Chinook Wool Felt Gambler Hat is part of Stetson's new John Wayne Collection of masculine and timeless designs. Featuring a stiff telescope crown, the Chinook is accented with a two-tone braided overlay leather hat band and metallic side pin. The hat's interior boasts a supple leather sweatband and…

$139.00
Available Colors:
  • BLACK

…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,…

(7)
$54.00
Available Colors:
  • BLACK

  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…

(11)
$59.00
Available Colors:
  • BLACK

  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® finish that…

(6)
$84.00
Available Colors:
  • BLACK

…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 interior boasts a supple genuine cowhide leather sweatband and Stetson…

(2)
$149.00
Available Colors:
  • NATURAL

…this fall, the Tellus Wool Felt Gambler Hat by Stetson. Part of their Seeker collection, this hat is made in the USA of 100% wool felt. The standout detail, the multicolored beaded hat band, is handmade, as is the beaded side pin. With a firm build and a genuine leather sweatband, this is a hat that…

$179.00
Available Colors:
  • PECAN

…resistant to cracking while still retaining the classic Panama hat look and feel. Pantropic's Twisted Panama Straw Gambler features a classic telescope crown trimmed with a genuine leather hat band and a relaxed, rolled overwelt brim.    Approx. 4" Telescope Crown 3 1/4" Rolled Overwelt…

$87.32
Available Colors:
  • BLACK

…the leather hat band matches the leather sweatband, making for one beautiful, quality gambler.   Approx. 4 1/4" Telescope Crown 4 1/4" Stiff Brim   Made of: 100% Wool Felt   Made in the USA Charlie 1 Horse Branding Leather Hat Band Metal Accents Leather Sweatband…

$159.00
Available Colors:
  • PECAN

…Long Oval Gambler Hat features a 100% shantung straw with a firm and structured finish. A long oval telescope crown and flared brim gives this gambler just the right blend of sophistication and ease. The gorgeous 10X Shantung Straw Long Oval Gambler Hat comes with a genuine leather hat band wih…

$136.00
Available Colors:
  • NATURAL

…  Seager's Los Dos Palm Straw Buckaroo Gambler Hat features the shape of the Americanized version of the vaquero or Mexican herders with a flat brim and telescope crown. The Los Dos in particular adds some simple twists such as a 1" leather hat band and Seager horseshoe pin. Made in the…

$120.00
Available Colors:
  • NATURAL

  Made in the USA   The Tribe Merino Wool Felt Gambler Hat is a stunning piece in the Biltmore's Hunt Club collection. Made in the USA of premium Merino wool felt, the Tribe is adorned with a tribal wax stitch leather hat band and Biltmore metal hat pin. Blocked with a stiff build…

$190.00
Available Colors:
  • BLACK

…Brim Toyo Straw Gambler Hat by Jeanne Simmons! Boasting the highest UPF sun protection rating possible (UPF 50+) with an extra wide brim, the Wide Brim Gambler has you (literally) covered from damaging UV rays. Its casual and functional design also includes a braided faux leather hat band and toggle…

(1)
$36.00
Available Colors:
  • NATURAL

…Finished in the USA   Quality matters to Sunbody Hats, and that's why they're proud  to showcase the Golf Guatemalan Palm Leaf Straw Gambler Hat. This impressive hat features a handcrafted palm straw build that's refined and stylish. The stylish cotton sweatband also doubles as a very…

(1)
$79.95
Available Colors:
  • NATURAL

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