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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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Telescope Gambler

1 - 28 of 33 Products
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  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)
$134.99
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

…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 eye-catching!   Approx. 4" Telescope

(1)
$189.95
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" Underwelt…

(21)
$59.95
Available Colors:
  • BLACK

…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 the interior boasts a leather sweatband. Made in Mexico of 100% toyo straw.   Approx. 3 3/4" Telescope Crown 3"…

$70.00
Available Colors:
  • BLACK

…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"…

$111.75
Available Colors:
  • NATURAL

…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 classic telescope crown and is…

(3)
$140.00
Available Colors:
  • TAN

…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!   Approx. 3 3/4" Telescope Crown 3…

$27.00
Available Colors:
  • TANBLACK

…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 3 1/4" Up-Turned Brim …

(4)
$160.00
Available Colors:
  • NATURAL

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 time!   Approx. 4" Telescope

$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

…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 detail for a handsome and elegant finish.    Approx. 3 3/4" Telescope Crown 3 3/8" - 3…

(2)
$154.99
Available Colors:
  • NATURAL

  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

…crown allows 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 -…

$174.99
Available Colors:
  • NATURALTAN

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

(7)
$99.95
Available Colors:
  • NATURAL

  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

…sweatband wicks away moisture to help keep you cool and dry. Look no further 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+…

$54.95
Available Colors:
  • NATURAL

…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   Made of: 100% Wool Felt   Made in the USA Firm/Stiff Body Charlie 1 Horse Branding…

$135.99
Available Colors:
  • PECAN

  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…

$145.00
Available Colors:
  • BLEACH

  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

…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 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.   Approx. 4" Telescope Crown 3 1/4" Curved Brim   Made of: 100% Twisted Seagrass   Leopard…

(6)
$56.00
Available Colors:
  • NATURAL

  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

…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" Telescope Crown 3"…

$154.99
Available Colors:
  • NATURAL

…of this gambler but the body of this hat should not go unnoticed. With a sharp telescope crown and rolled brim, it's amazing how Toucan created such exquisite lines while still maintaining a flexible build. A stellar headwear option from Toucan Collection.   Approx. 4" Telescope Crown 3…

$128.00
Available Colors:
  • BROWN
  • LODEN

…that easily adjusts the hat's fit. Great for any outdoor activities, the Wide Brim Gambler by Jeanne Simmons has the coverage you need in a stylish and functional design you'll love.    Approx. 3 1/4" Telescope Crown 5 1/8" Floppy Brim   Made of: 75% Toyo Straw 25% Polyester …

(2)
$40.00
Available Colors:
  • NATURAL

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