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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 Hat

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…intended fit of the 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…

(29)
$39.95

  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 flared, upturned brim. Made in the USA by expert craftsmen, the Joker features their exclusive wool LiteFelt® finish that…

(3)
$75.60

…Scars Wool 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.   …

$144.00

  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"…

(14)
$49.95

…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…

(49)
$90.00

…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 stiff finish, the…

(4)
$36.00

…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…

(3)
$120.00

…3/8 XL = 7 5/8   Made in the USA   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…

(5)
$81.00

…    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…

$120.00

…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…

(1)
$120.00

…golf course with the stylish Back Nine Raffia Straw Gambler Hat by Kenny K! Made of lightweight raffia straw in a classic gambler hat design, the Back Nine Gambler features a telescope crown and wide, upturned brim. A 3-pleat, tropic printed hat band encircles the crown for a casual finish that goes…

(2)
$24.00

…Felt Gambler Hat from Charlie 1 Horse is a high-quality 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.

$135.00

  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…

(2)
$110.00

…  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)
$76.00

…flair to your wardrobe with the Phoenix Black Wool Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most notably, the grosgrain ribbon hat band features an adornment of fringe that's incredibly…

$99.00
Available Colors:
  • BLACK

  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…

(2)
$48.00

…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 build, this gambler is perfect for any time spent outside this season! …

$30.00

  UPF 50+   Handwoven in Ecuador, Finished in the USA There are men and women that just feel right in a gambler style panama hat, and for those people, the UPF 50+ Trinidad is the best offering. The unisex Pantropic Trinidad - a lightweight toquila palm-based weave - can finish…

(1)
$144.00

…flair to your wardrobe with the Phoenix Ivory Wool Felt Gambler Hat from Brixton Hats! This comfortable hat features a wool felt body with a grosgrain ribbon sweatband and breathable, unlined interior. Most notably, the grosgrain ribbon hat band features an adornment of fringe that's incredibly…

$99.00
Available Colors:
  • IVORY

Hat offers an elegant and classic style in lightweight and breathable Toyo straw. Featuring a black grosgrain ribbon hatband and 3-inch, slightly upturned brim, this timeless hat is finished with an elastic cotton sweatband. Perfect for spring and summer - the Conner Deluxe Toyo Straw Gambler Hat

$56.00

UPF 50+   It's difficult to think of a finer hat than the Madrid Laminated Toyo Gambler Hat from Head 'N Home. This stunning hat features a breathable telescope crown, as well as a hand embossed leather hat band. Additionally, the stiff laminated finish allows for a firm, durable…

$57.00

hat's inner tag. This was a manufacturing error. Size M/L fits between sizes 7 1/8 - 7 1/4.    Handwoven in Ecuador; Blocked & Finished in the USA   Made of twisted genuine Panama straw, Pantropic's Twisted Panama Straw Gambler Hat features a loose weave in a classic gambler

$111.00

…Brim Toyo Straw Gambler Hat by Jeanne Simmons! Boasting the highest UPF sun protection rating possible (UPF 50+) with an extra wide brim, the Wide Brim Gambler has you (literally) covered from damaging UV rays. Its casual and functional design also includes a braided faux leather hat band and toggle…

$34.00

…original hat size.   Handwoven in Ecuador; Blocked & Finished in the USA   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)
$88.00
Available Colors:
  • NATURAL

…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…

$138.00

…enjoys relaxing bayside or taking part in outdoor activities. 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" Crown 3 1/4" Brim   Made of:…

(4)
$36.50

  Conner's Hemp Gambler Hat is a great piece for those that prefer a more structured item. The hemp material keeps the weight of the hat light but continues to give protection from the elements.   Approx. 4" Crown 2 3/4" Brim   Made of: 100% Hemp   Lined Cotton…

$50.00

  Made in the USA   The Stetson Pin Seeker Hemp Straw Gambler Hat boasts a distinctive and handsome aesthetic not often seen in gambler styles. Crafted of premium hemp braid right here in the USA, the Pin Seeker is an ode to expert craftsmanship and exudes elegance in its simplicity.…

$110.00

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