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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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Gambler

1 - 28 of 33 Products
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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…

(10)
$53.10
Available Colors:
  • BLACK
  • BROWN

…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)
$76.00
Available Colors:
  • NATURAL

  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…

(1)
$144.00
Available Colors:
  • BLACK

  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)
$44.96
Available Colors:
  • BLACK

…Shantung Straw 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…

$136.00
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)
$99.00
Available Colors:
  • TAN

…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 of crushable wool felt. Adorned with a faux leather hat band overlaid with feathers, the Kelso…

(5)
$89.10

  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® finish that…

(5)
$75.60
Available Colors:
  • BLACK

…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 Black Wool Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most…

$89.10
Available Colors:
  • BLACK

…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 hat style. Handwoven in Ecuador then blocked and finished in the USA, this style represents hours of artisanal work…

$87.32
Available Colors:
  • DARKNATURAL
  • NATURAL
  • BLACK

  Crafted 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…

(7)
$45.00
Available Colors:
  • BLACK

…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…

(51)
$89.10
Available Colors:
  • BLACK

  Made in the USA   The Stetson Seeker Collection presents the Batterson Wool Felt Gambler Hat. The Batterson features firm wool felt, a vegan leather sweatband and a satin lining. The pièce de résistance is the multi-wrapped cotton cord hat band with faux gem fastening accent. A…

$142.20
Available Colors:
  • SAND

…the sun off and look your best on the golf course with the stylish Back Nine Raffia Straw Gambler Hat by Kenny K! Made of lightweight raffia 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…

(4)
$24.00
Available Colors:
  • BLACK

  Made in the USA     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…

$126.00
Available Colors:
  • NATURAL

  Made in the USA   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…

(1)
$130.00
Available Colors:
  • NATURAL

  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! …

(3)
$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…

(2)
$48.00
Available Colors:
  • NATURAL

…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 Ivory Wool Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most…

$89.10
Available Colors:
  • IVORY

  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 summer -…

$63.00
Available Colors:
  • IVORY

…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 you cool on those hot summer…

(7)
$88.00
Available Colors:
  • NATURAL

…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

…  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 3-pleat cotton headband and an elasticized terrycloth…

(32)
$39.95
Available Colors:
  • SEAGRASS

  Made in the USA   The John Wayne 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…

$112.50
Available Colors:
  • BLACK

…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.

$135.00
Available Colors:
  • PECAN

  Made in Mexico   Charlie 1 Horses' gambler for the 2020 Fall/Winter season, the Happy Trails Wool Felt Gambler Hat. Part western, part outback, a gambler is known for its distinct oval crown and wide brim and the Happy Trials carries on that tradition but with a little twist via its…

$142.20
Available Colors:
  • SILVERBELLY

…and class 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…

$138.00
Available Colors:
  • NATURAL

…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 with a grosgrain ribbon sweatband and a breathable, unlined interior. Most…

$85.50

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