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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

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…Made in the USA   A standout piece, made by the always fashionable and chic, Renegade by Bailey, the Cowpuncher Wool and Angora Felt Gambler Hat. Crafted from soft angora and wool with a felt finish, this ultra-trendy look also features an extra wide grosgrain ribbon hat band, antique…

$180.00

…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…

(3)
$119.99
Available Colors:
  • SILVERBELLY

  Made in the USA   Gorgeous and striking, a perfect staple this spring, the Tellus Shantung Straw Gambler Hat by Stetson. This hat is made in the USA of 100% shantung straw. The standout detail, the multicolored seed bead hat band, is handmade, as is the beaded side pin. With a firm…

$131.20
Available Colors:
  • CHOCOLATEBROWN

…straw that does Stetson proud, the Highlands Palm Straw Gambler Hat! The craftmanship of the braided palm straw is more than enough on its own but Stetson doesn't skimp where design is concerned. A leather hat band is wrapped around the crown featuring metal studs and an embossed Stetson logo. The…

$94.99
Available Colors:
  • NATURAL

…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" Flat Brim   Made of: 100% Wool Felt   Made in the USA Firm/Stiff Body Charlie 1 Horse Branding…

$135.99
Available Colors:
  • PECAN

  Crafted with a telescope crown and curved 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…

(9)
$65.00
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…

(2)
$128.99
Available Colors:
  • BLACK

…Leather Conch Band Wool Felt Gambler Hat is a fancy piece without the fancy price tag. The gambler keeps it shape without compromising the comfort of the hat. Be prepared, you will be receiving a lot of compliments when you wear this hat.   Approx. 4" Telescope Crown 3" Underwelt Brim …

$98.00
Available Colors:
  • BLACK

  Made in the USA   Gorgeous and striking, a perfect staple 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…

(1)
$179.00
Available Colors:
  • PECAN

…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 5/8" Telescope Crown 3 3/8" Underwelt…

(21)
$59.95
Available Colors:
  • BLACK

  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…

(4)
$61.95
Available Colors:
  • NATURAL

  Made in the USA Introducing the Joker Wool LiteFelt® Gambler Western Hat by Renegade. This is a great wool gambler with a stylish studded leather hat band and curved brim. Made in the USA by expert craftsmen, the Joker features their exclusive wool LiteFelt® finish that makes this…

(6)
$110.00
Available Colors:
  • BLACK

  Made in Mexico   A new and stunning headwear offering from Charlie 1 Horse, the Mamacita Palm Straw Gambler Hat. A tight and attractive braided palm straw body is accented with a seed bead hat band. This hat band is a true celebration of color and is further accented with a concho…

$95.20
Available Colors:
  • NATURAL

…The card suit, spade (based upon the medieval weapon, the halberd) lends itself to a distinct and unique crown. A flat pencil curl brim pairs nicely with the spade crown, it pays homage to a gambler hat. The double layer trim has a playful print puggaree hat band with a leather lace overlay. No need…

$180.00
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…

(13)
$70.00
Available Colors:
  • BLACK
  • BROWN

  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…

(4)
$59.95
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…

(3)
$134.99
Available Colors:
  • BLACK

…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 hat band and an elasticized terrycloth sweatband for an easy comfortable fit. The underbrim and crown

(35)
$49.95
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

(1)
$189.95
Available Colors:
  • NATURAL

…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…

(2)
$154.99
Available Colors:
  • NATURAL

…tint to it and appears more brown than green.   Made in the USA   The Lang Elite Wool Felt Gambler Hat has a distinct teardrop crown, a mix of a telescope crown with a soft point. Bailey 1922 creates the elite finish with fine 16 micron sheep's wool, that undergoes carding…

$187.00
Available Colors:
  • BLACK
  • DENIMBLUE
  • ARMYGREEN

…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…

(10)
$119.99

…the Golf Guatemalan Fine Palm Leaf Straw Gambler Hat. This impressive hat features a handcrafted palm straw body 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" Pencil Curl Brim   Made…

(1)
$63.96
Available Colors:
  • NATURAL

…distressed, matte finish. The brim is shorter while the crown is higher, giving off a bit more of a conservative look. The braided leather hat band and tassel accent add just a touch of style.     Approx. 3 7/8" Gambler Crown 2 1/2" Curved Brim   Made of: 100% Genuine…

(2)
$75.00

…this gambler but the body of this hat should not go unnoticed. With a sharp telescope crown and rolled brim, it's amazing how Toucan created such exquisite lines while still maintaining a flexible build. A stellar headwear option from Toucan Collection.   Approx. 4" Telescope Crown 3 1/4"…

$128.00
Available Colors:
  • BROWN
  • LODEN

…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 body, this gambler is perfect for any time spent outside this season!   Approx. 3 3/4" Telescope Crown 3…

$25.50
Available Colors:
  • TANBLACK

…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…

(3)
$140.00
Available Colors:
  • TAN

…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   …

(4)
$160.00
Available Colors:
  • NATURAL

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