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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

1 - 28 of 41 Products
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…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…

(8)
$92.65

  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…

(12)
$59.50
Available Colors:
  • BLACK
  • BROWN

…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…

(1)
$92.65
Available Colors:
  • SILVERBELLY

…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…

(55)
$92.65
Available Colors:
  • BLACK

…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…

(2)
$93.50
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…

(3)
$50.96
Available Colors:
  • BLACK

…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   Made of: 100% Wool Felt   Made in the USA Charlie 1 Horse Branding Leather Hat Band…

$151.30
Available Colors:
  • PECAN

…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)
$143.65
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)
$152.15
Available Colors:
  • PECAN

…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   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…

$131.75
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…

(7)
$55.25
Available Colors:
  • BLACK

…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…

$170.00
Available Colors:
  • BLACK
  • DENIM
  • ARMYGREEN

…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…

$127.50

…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 Crown

(19)
$50.96
Available Colors:
  • BLACK

  Made in the USA   UPF 50+ Sun Protection   The Large Brim Toyo Straw Gambler Hat from the Toucan Collection is an updated western staple. The breathable toyo straw body provides great sun protection without weighing heavy upon your head. The simple grosgrain ribbon hat…

$54.40
Available Colors:
  • BLACK

…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)
$106.25
Available Colors:
  • NATURAL

…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 3/4" Telescope Crown 3 3/4"…

$126.65
Available Colors:
  • NATURAL

…Handwoven, Blocked, and Finished in Ecuador   A beautiful panama straw 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…

$123.25
Available Colors:
  • NATURAL

…The Tribe 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 telescope crown and flat brim.   …

$114.00
Available Colors:
  • BLACK

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

$140.00
Available Colors:
  • NATURAL

…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 sweatband also doubles as a very comfortable addition!   Approx. 4 1/4" Telescope Crown 3 3/4" Pencil Curl Brim   Made…

(1)
$67.96
Available Colors:
  • NATURAL

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

(34)
$42.46
Available Colors:
  • SEAGRASS

  Made in the USA Introducing the Joker LiteFelt® Wool 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)
$80.75
Available Colors:
  • BLACK

…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   Made of: 100% Genuine Leather   Packable/Crushable Build Matte Finish 4 Metal Grommet Eyelets - For…

(1)
$67.96
Available Colors:
  • BROWN
  • BLACK

…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 you cool on those hot summer days!   Approx. 4" Telescope Crown 3 1/4" Underwelt Brim   Made of: 100% Genuine…

(7)
$84.96
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)
$126.65
Available Colors:
  • NATURAL

…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 and breathability.   Approx. 4" Telescoping Crown 3"…

$118.15
Available Colors:
  • NATURAL

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