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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-Hat

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  Handwoven in Ecuador; Blocked and Finished in the USA   Quality 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,…

(1)
$189.95
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…

(2)
$154.99
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 5/8" Telescope Crown 3 3/8"…

(21)
$59.95
Available Colors:
  • 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)
$160.00
Available Colors:
  • NATURAL

  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

  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

  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 Mexico   A durable 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…

$94.99
Available Colors:
  • NATURAL

  Made in Mexico   Since 1929, Eddy Bros has been making quality hats with style and class and the same goes for the Reed Toyo Straw Gambler Hat. This gambler has a stiff body with the classic telescope crown and dramatically curved brim. The hat band is made of leather with metal…

$70.00
Available Colors:
  • BLACK

  Handwoven in Ecuador; Blocked and Finished in the USA   The Kalama Panama Straw Gambler Hat by Tommy Bahama features the classic telescope crown. This wide brim Panama hat will keep you protected from the sun while out in style. The elasticized COOLMAX® sweatband is so comfortable,…

$111.75
Available Colors:
  • NATURAL

  Please Note: This style features a printed overlay hat band in either blue or green. This is an assorted feature that cannot be selected for.    UPF 50+ Sun Protection   The Golf Toyo Straw Gambler Hat by Dorfman Pacific Company is a classic warm-weather style ideal for…

$54.95
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…

(3)
$140.00
Available Colors:
  • TAN

  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   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

  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

  Please Note: Sizes run large. We recommend ordering 1 size below your original hat size.   Bodies Handwoven, Blocked & Finished in Ecuador   Whether you're headed to the beach or just shading yourself in style, the Jaxon Gambler Cuenca Grade 3 Panama Hat is the…

(7)
$99.95
Available Colors:
  • NATURAL

  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)
$159.00
Available Colors:
  • BLACK

  Handwoven, Blocked, and Finished in Ecuador   Part western, part outback, the Panama Straw Grade 10 Gambler Hat by Hats Montecristi features a distinct telescope crown and wide brim. Handwoven, this is a grade 10 panama which denotes a fine weave giving it a flexible, soft and…

$123.25
Available Colors:
  • BLEACH

  Perfect for the woman with fashion sense, who enjoys relaxing bayside or taking part in outdoor 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. …

(6)
$56.00
Available Colors:
  • NATURAL

  Conner's 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"…

$98.00
Available Colors:
  • BLACK

  Please Note: The color 'Army Green' has a very strong brownish 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…

$187.00
Available Colors:
  • BLACK
  • DENIMBLUE
  • ARMYGREEN

  Made in the USA   The High Desert Wool 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…

$178.00
Available Colors:
  • PECAN

  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 interior,…

$139.99
Available Colors:
  • NATURAL

  Made in the USA   Travel back in time with a deck of cards with Bailey's Ganon Elite Wool Felt Gambler Hat. It has a stiff finish, and its brim has been whipstitched for a polished look. Uniquely crafted with a leather hat band and a Bailey logo metal bar, the Ganon will make you…

$199.75
Available Colors:
  • BLACK
  • BONE

  Please Note: This style has a shallow fit. This is the 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…

(35)
$49.95
Available Colors:
  • SEAGRASS

  With the 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 curved brim and intricate telescope crown gives a classic silhouette while the black layered cotton twill hat…

(3)
$49.95
Available Colors:
  • IVORY

  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

  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,…

$180.00

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