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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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Mens Gambler Hats

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…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

  Jaxon Hats' newest leather hat, the Crusher Leather Outback Hat, is made of 100% genuine leather with a gorgeous polished finish. 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…

(1)
$79.95
Available Colors:
  • BROWN
  • BLACK

…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…

(57)
$119.99
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 5/8" Telescope Crown 3 3/8"…

(21)
$59.95
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

…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 this hat.   …

(2)
$128.99
Available Colors:
  • BLACK

  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

…with a soft, unstructured crown is accented with an embroidered Kangol logo at its front and a sleek leather adjustable strapback. Ideal for both men and women, the Washed Cotton Ball Cap is outrageously comfortable and has that trending "dad cap/hat" appeal.    Approx. 4" Crown 2 5/8"…

$45.00

  FINAL SALE   Everyone is a Winner!!   Approx. 2 5/8" Bill/Visor   Made of: 100% Cotton   Cotton Sweatband Hook and Loop Adjustable Strap 6 Eyelets Unlined   Size: Adjustable - Fits sizes 6 7/8 (S) - 7 1/2 (XL) comfortably using adjustable hook…

$9.95
Available Colors:
  • ROYALBLUEGOLD

…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 copper star concho accent and grosgrain ribbon binding on the brim.…

$180.00

…UPF 50+ Sun Protection   It's hard to find a finer hat than the Wool Felt Rancher Fedora Hat from Lack of Color. This stylish hat is designed in Australia, featuring a gorgeous wool felt wide brim body, with a grosgrain ribbon hat band wrapping around the teardrop crown. Additionally, the…

$111.75
Available Colors:
  • FORESTGREEN

  Designed with on-the-go in mind, the Wyatt Wool Felt Western Cowboy Hat by Jaxon Hats is finished with a packable/crushable body. A faux leather hat band with braided detailing and silver concho accent adorns the crown. Also features a Jaxon side pin, cotton twill sweatband and is…

(1)
$59.95
Available Colors:
  • BLACK

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 of stiff seagrass, the gambler features a handsome 3-pleat cotton hat

(35)
$49.95
Available Colors:
  • SEAGRASS

Hat is perfect for any warm weather outing while the Classic Cotton Ivy Cap can be worn from spring until late fall. And the 100% wool C-Crown Crushable Fedora for crisper days.   Discover Hiker Cotton Outback Hat by Torrey Hats  Classic Cotton Ivy Cap by Jaxon Hats  …

$71.96

…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, well-made gambler. Additionally, the grosgrain ribbon hat band and Scala metal side pin are undeniably…

(1)
$189.95
Available Colors:
  • NATURAL

…K has struck gold with the Two-Tone Toyo 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! …

$25.50
Available Colors:
  • TANBLACK

…  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

…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 perfect choice. Lightweight with consistent weaving, this Panama Hat will keep…

(7)
$99.95
Available Colors:
  • NATURAL

…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

  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

…  The Batterson Shantung Straw Gambler Hat by Stetson is reminding people that details do matter. Its woven shantung straw in an alternating tonal pattern and vented crown allows for a simple gambler to become unique and complex. The cotton cord hat band with a faux gem fastening accent…

$174.99
Available Colors:
  • NATURALTAN

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 the season. Crafted of twisted toyo straw, the Golf Gambler

$54.95
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

…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

…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!   Approx. 3 1/2" Telescope Crown…

(4)
$160.00
Available Colors:
  • NATURAL

  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

…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
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