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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 Crowns

1 - 27 of 27 Products
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…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" Telescope Crown

(14)
$42.46
Available Colors:
  • BLACK

  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…

$125.00
Available Colors:
  • BLACK

…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 crown. Live the life of luxury with…

$160.00
Available Colors:
  • BLACK

…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 and breathability.   Approx. 4" Telescoping Crown 3"…

$126.00
Available Colors:
  • NATURAL

  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…

(6)
$50.00
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…

(7)
$59.00
Available Colors:
  • BLACK

…just cannot be ignored. Additionally, 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…

$150.00
Available Colors:
  • PECAN

…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 days!   Approx. 4" Telescope Crown 3 1/4" Underwelt Brim   Made of: 100% Genuine…

(7)
$74.80
Available Colors:
  • NATURAL

…with an elastic cotton sweatband. Perfect for spring and summer - the Conner Deluxe Toyo Straw Gambler Hat easily dresses up or down to compliment your warm-weather wardrobe.    Approx. 4 1/4" Crown 3" Upturned Brim    Made of: 100% Toyo Straw   Grosgrain Ribbon Hatband…

$63.00
Available Colors:
  • IVORY

…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 notably, the grosgrain ribbon hat band features an adornment of fringe that's incredibly stylish!   Approx. 4" Telescope Crown 3…

$95.00

…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 comfortable addition!   Approx. 4 1/4" Telescope Crown 3 3/4" Up-Turned Brim   Made…

(1)
$76.00
Available Colors:
  • NATURAL

…the Madrid Laminated Toyo Gambler Hat from Head 'N Home. This stunning hat features a breathable telescope crown, as well as a hand embossed leather hat band. Additionally, the stiff laminated finish allows for a firm, durable build.   Approx. 4" Telescope Crown 3 1/2" Stiff Brim …

$57.00
Available Colors:
  • CREAM

…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 season!   Approx. 3 3/4" Telescope Crown 3…

$30.00
Available Colors:
  • TANBLACK
  • WHITEBLACK

…LONG OVAL crown which results in a longer and narrower fit. Updated sizing for the style is listed below or you may call us at 1-888-847-4287 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…

(5)
$95.00

…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 3…

(49)
$95.00
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…

(4)
$71.40
Available Colors:
  • BLACK

…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 3 1/4" Up-Turned Brim   …

(3)
$120.00
Available Colors:
  • NATURAL

…Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most notably, the grosgrain ribbon hat band features an adornment of fringe that's incredibly stylish!   Approx. 4" Telescoping Crown 3…

$99.00
Available Colors:
  • BLACK

…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 crown tip…

(1)
$130.00
Available Colors:
  • NATURAL

…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 sweatband for an easy comfortable fit. The underbrim and crown

(32)
$33.96
Available Colors:
  • SEAGRASS

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 eye-catching!   Approx. 4" Telescope Crown

$138.00
Available Colors:
  • NATURAL

  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   Lined Cotton…

$57.00
Available Colors:
  • CAMEL

…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 Brim    Made of: 100% Genuine Panama…

$111.00
Available Colors:
  • DARKNATURAL
  • NATURAL
  • BLACK

…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 classic telescope crown and is…

(2)
$110.00
Available Colors:
  • TAN

…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 horseshoe-creased crown. An embossed…

$158.00
Available Colors:
  • SILVERBELLY

…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   Made of: 100% Twisted Seagrass   Leopard Scarf…

(5)
$36.50

…Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most notably, the grosgrain ribbon hat band features an adornment of fringe that's incredibly stylish!   Approx. 4" Telescoping Crown 3…

$99.00
Available Colors:
  • IVORY

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