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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 (32)

Small Brim Gambler Hats

1 - 28 of 32 Products
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…Crown - Back 3" Curved 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 with Star Side Pin Small Wooden Bailey Side Pin DRI-LEX®…

(3)
$140.00
Available Colors:
  • TAN

…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, you'll wear this hat all day long!   Approx. 3…

$111.75
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 body with the classic telescope crown and dramatically curved brim. The hat band is made of leather with metal concho accents while…

$70.00
Available Colors:
  • BLACK

…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 Brim

(21)
$59.95
Available Colors:
  • BLACK

…than the Golf Toyo Straw Gambler Hat by Dorfman Pacific to keep you cool this spring/summer!   Approx. 4" Telescope Crown 3 1/2" Flat, Curled Underwelt Brim   Made of: 100% Toyo Straw   UPF 50+ Sun Protection Lightweight & Breathable Web Hat Band with Print Overlay…

$54.95
Available Colors:
  • NATURAL

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" Pencil Curl Brim   Made of: 100% Wool Felt   Packable Conch & Faux Leather Hat Band Underwelt Brim

(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 metallic…

(4)
$59.95
Available Colors:
  • BLACK

…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

…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 body and a DRI-LEX® sweatband, this is a hat that will stand the test of…

$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

…  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…

$94.99
Available Colors:
  • NATURAL

…for a simple gambler to become unique and complex. The cotton cord hat band with a faux gem fastening accent adds another layer of charm. With the removable side feather, you can decide just how many extra details you desire.    Approx. 4” Telescope Crown 3 1/4" Flat Brim - Front &…

$174.99
Available Colors:
  • NATURALTAN

…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 ribbon hat band. The Colonel's…

(2)
$154.99
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)
$160.00
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 body 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…

$95.20
Available Colors:
  • NATURAL

…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 supple feel. Features a grosgrain ribbon hat band. Comfortable and elegant, you are…

$145.00
Available Colors:
  • BLEACH

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" Flat Brim

$135.99
Available Colors:
  • PECAN

…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…

$98.00
Available Colors:
  • BLACK

  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

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 style both packable/crushable and water repellent. No stiff hats here!…

(6)
$110.00
Available Colors:
  • BLACK

…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 stand out!   Approx. 4" Teardrop Crown 3" Flat Brim   Made of: 100%…

$199.75
Available Colors:
  • BLACK
  • BONE

…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, allowing for comfort…

$154.99
Available Colors:
  • NATURAL

hat band and metallic side pin. The hat's interior boasts a supple leather sweatband and custom satin lining. Crafted proudly in the USA, the John Wayne Chinook Wool Felt Gambler Hat is sure to serve you well for years to come.   Approx. 4 1/4" Telescope Crown 3 1/2" Curved Brim

(3)
$134.99
Available Colors:
  • BLACK

…finish. The Lang Elite Wool Felt Gambler Hat is then treated with a 'hand-cooked' shellac for the heritage stiffened touch. No detail has been overlooked on the Bailey 1922 Lang Elite Wool Felt Gambler Hat.   Approx. 4 1/4" Teardrop Crown 3" Snap Brim   Made of: 100% Wool…

$187.00
Available Colors:
  • BLACK
  • DENIMBLUE
  • ARMYGREEN

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

(10)
$119.99

…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 copper star concho accent and grosgrain ribbon binding on the brim. Take your boho western aesthetic to the…

$180.00

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" Curved Brim

(57)
$119.99
Available Colors:
  • BLACK

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