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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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Extra Large Gambler Hats

1 - 25 of 25 Products
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…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…

(7)
$50.00
Available Colors:
  • BLACK

…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)
$99.00

…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 are undeniably…

$138.00
Available Colors:
  • NATURAL

…tonal pattern and vented crown allows for a simple gambler to become unique and complex. The cotton cord hat band with a faux gem fastening accent adds another layer of charm. With the removable side feather, you can decided just how many extra details you desire.    Approx. 3 7/8”…

$168.00
Available Colors:
  • NATURALTAN

  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

…Note: Sizes run large. We recommend ordering 1 size below your 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…

(7)
$88.00
Available Colors:
  • NATURAL

  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"…

(15)
$49.95
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 metallic…

$52.00
Available Colors:
  • BLACK

…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!   Approx. 3 1/2" Telescope Crown…

(4)
$125.00
Available Colors:
  • NATURAL

  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)
$48.00
Available Colors:
  • NATURAL

…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…

(2)
$130.00
Available Colors:
  • NATURAL

  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…

(2)
$110.00
Available Colors:
  • TAN

hat's inner tag. This was a manufacturing error. Size M/L fits between sizes 7 1/8 - 7 1/4.    Handwoven in Ecuador; Blocked & 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

$87.32
Available Colors:
  • DARKNATURAL
  • NATURAL
  • BLACK

…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.    Constructed of stiff seagrass, the gambler features a handsome…

(32)
$39.95
Available Colors:
  • SEAGRASS

…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

(6)
$84.00
Available Colors:
  • BLACK

…Toyo Straw Gambler Hat - Black Band by Jaxon Hats, you won't have to take a gamble. This is a quality western made of a tightly woven toyo straw with a semi-stiff finish. The flared brim and intricate telescope crown gives a classic silhouette while the black layered cotton twill hat band adds…

(2)
$39.95
Available Colors:
  • IVORY

…    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…

$126.00
Available Colors:
  • NATURAL

…Please Note: Brixton sizes run large. See below or call us at 1-888-847-4287 for help with sizing. XS = 6 3/4 S = 7 M = 7 1/4 L = 7 1/2   Add a bit of flair to your wardrobe with the Phoenix Coconut Wool Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body…

$76.00

…  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 USA…

$120.00
Available Colors:
  • NATURAL

…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 a…

$136.00
Available Colors:
  • NATURAL

…  Handwoven in Guatemala; 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…

(1)
$79.95
Available Colors:
  • NATURAL

…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 crown. Live the life of luxury with this hat.   …

(2)
$160.00
Available Colors:
  • BLACK

…Toyo Straw Gambler Hat by Seager finds its history in the buckaroo hat which is the Americanized version of the headwear worn by vaqueros or Mexican herders. Often worn with a flat brim, the L'amour keeps this vaqueros tradition and also features a classic staple of the gambler hat, a telescope…

$140.00
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…

(53)
$99.00
Available Colors:
  • BLACK

  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…

$78.00
Available Colors:
  • BROWN
  • BLACK

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