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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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  • Retail (23)

Small Brim Gambler Hats

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…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 3 3/4" Brim with 1/2"…

$140.00
Available Colors:
  • NATURAL

…    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…

$139.00
Available Colors:
  • NATURAL

…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 flared brim and absorbent DRI-LEX® sweatband. Its…

(6)
$109.00

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.   Approx. 4 1/4" Telescope Crown 4 1/4" Stiff Brim

$159.00
Available Colors:
  • PECAN

  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)
$54.00
Available Colors:
  • BLACK

…  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

…Crown - Back 3" Flared Brim   Made of: 100% Toyo Straw with Raindura Finish - Water Resistant & Shape Retentive   Made in the USA Exclusive Raindura Finish - Maintains its shape even after getting wet! Braided Hat Band w/ Star Side Pin Small Wooden Bailey Side Pin DRI-LEX®…

(2)
$110.00
Available Colors:
  • TAN

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, you'll wear this hat all day long!   Approx. 3 3/4" Telescope Crown 3 3/4" Curled Brim

$149.00
Available Colors:
  • NATURAL

…  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 build with the classic telescope crown and dramatically flared brim. The hat band is made of leather with metal concho accents while…

$60.00
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" Telescope…

(18)
$49.95
Available Colors:
  • BLACK

…finish, the Western Gambler is accented with a western-inspired conch faux leather hat band tied at the side. Unlined for better packability, the Western Gambler is finished with a cotton sweatband.    Approx. 3 5/8" - 3 3/4" Telescope Crown 3 1/2" Upturned, Underwelt Brim   Made…

(12)
$59.00
Available Colors:
  • BLACK
  • BROWN

…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 Panama…

(7)
$99.95
Available Colors:
  • NATURAL

…  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 metal studs and an embossed…

$76.00
Available Colors:
  • NATURAL

…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   Made of:…

(4)
$125.00
Available Colors:
  • NATURAL

…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 pin. With a firm build and a genuine leather sweatband, this is a hat that will stand the…

(1)
$179.00
Available Colors:
  • PECAN

…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 accent with faux turquoise cabochon and leather embossed feather. Every detail of this hat showcases the…

$112.00
Available Colors:
  • NATURAL

…with a gambler silhouette, Bigalli has made another stunner with the Harlow Vented Panama Straw Gambler Hat. With a telescope crown and flat brim, we love this look paired with the expert craftmanship needed to weave a panama straw hat. Our favorite part, the enviromentally concious hat band made…

$145.00
Available Colors:
  • NATURAL

…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   Made…

$94.00
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…

(3)
$39.95
Available Colors:
  • IVORY

…Merino Wool Felt Gambler Hat is a stunning piece in the Biltmore's Hunt Club collection. Made in the USA of premium Merino wool felt, the Tribe is adorned with a tribal wax stitch leather hat band and Biltmore metal hat pin. Blocked with a stiff build tear drop crown and flat brim.   …

$190.00
Available Colors:
  • BLACK

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 1/2" Underwelt Brim

(55)
$109.00
Available Colors:
  • BLACK

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 1/2" Underwelt Brim

$109.00
Available Colors:
  • SILVERBELLY

…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 from the norm, the Crusher Leather Outback Hat is a perfect fit.   Approx. 3 3/4" Gambler Crown 3" Polywire Brim   …

(1)
$78.00
Available Colors:
  • BROWN
  • BLACK

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