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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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Men Gambler Straw Hats

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…need a new beach hat, a hat for the outdoors or just a great looking, all-around sun hat - the Trinidad Toyo Straw Gambler Hat is for you!   Approx. 4 1/2" Telescope Crown 4" Upturned Overwelt Brim   Made of: 100% Toyo Straw (Paper)   Wide Brim Gambler Shape Vent-Weave…

$72.00
Available Colors:
  • TAN

…best on the golf course with the stylish Back Nine Straw Gambler Hat by Kenny K! Made of lightweight 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…

$24.00
Available Colors:
  • BLACK

Straw Gambler 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

$49.00
Available Colors:
  • IVORY

…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…

$108.00
Available Colors:
  • NATURAL

…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 Straw (Cuenca weave -…

$88.00
Available Colors:
  • NATURAL

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

$148.00
Available Colors:
  • DARKNATURAL
  • NATURAL

  Made in the USA   A classic gambler style with a western edge, the Rockett Toyo Straw Gambler Hat by Bailey features their exclusive new Endura Finish which helps the hat maintain its shape even after getting wet. Pliable and completely packable, Rockett has a crease down its…

$100.00
Available Colors:
  • TAN

…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…

$39.95
Available Colors:
  • SEAGRASS

…style, the Jaxon Gambler Cuenca Grade 3 Panama Hat is the perfect choice. Lightweight with consistent weaving, this tan Panama Hat will keep you stylish and cool on those hot summer days! Approx. 4" Crown 3 1/4" Underwelt Brim   Made of: 100% Genuine Panama Straw (Cuenca Weave -…

$85.00
Available Colors:
  • TAN

  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.…

$148.50
Available Colors:
  • NATURALOLIVE

  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…

$43.00
Available Colors:
  • CAMEL

…Cotton Gambler Hat is a dapper alternative to the standard pinch front/tear drop crowned Safari/Aussie/Outback styles so pervasive in the outdoor hat market. The Stetson Distressed Gambler Hat features a telescope crown stylishly bisected by a seam and adorned with a simple, self-fabric hat band and…

$57.60
Available Colors:
  • BROWN

…  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…

$40.00
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 3/8" Underwelt Brim 3 5/8"…

$49.95
Available Colors:
  • BLACK

…classy, the Cheetah Wool Felt Gambler Hat from Hatch has it all. It features a faux leather hat band, brought together with a metallic buckle, which match the wool felt design perfectly. The cheetah print design is just the perfect bow tying together this masterpiece of a hat.   Approx. 4"…

$65.00

  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 though you will be receiving a lot of compliments when you wear this piece.   Approx. 4" Crown 3"…

$58.00
Available Colors:
  • BLACK

…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:…

$45.00
Available Colors:
  • NATURAL

…Wool Gambler Hat from Scala. The focus of this clean hat is the intriguing hat band, a beautiful combination of stitched colors and extra decoration. Fun and flirty, this hat has it all!   Approx. 3 1/2" Crown 3 5/8" Floppy Brim   Made of: 100% Wool   Intricate Hat Band…

$50.00
Available Colors:
  • CAMEL

…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.   …

$160.00
Available Colors:
  • BLACK

FINAL SALE Bag o’ Beanie Hats, you love them, hell we all love them. We have what you need, a plethora of beanies in all styles, colors, and brands. A $30 purchase nets you $60 worth of beanies; quite possibly enough beanies to last you the rest of your days. You will receive an assortment of…

$24.95
Available Colors:
  • MULTI

…value bag includes everything from boaters to wide brim sun hats. You can feel like you are among the gondolas of Venice, or Blanche DuBois in your elegance wide brimmed sun hat. The real excitement is anticipation the arrival of new hats, we choose the assortment. Now that is true excitement, not…

$49.95
Available Colors:
  • MULTI

…articles.   Introducing the Outback Trading Company Duck Back Dressing. It is a waterproof cream that is very simple to apply to Oilskin hats, and directions are right on the bottom of the container.   Manufacturer Instructions for Use: * Best Results are obtained when…

$12.95

  Made in the USA Introducing the Honey Straw Western Hat by Renegade. This is a gorgeous straw gambler western hat. The leather hat band is put together by pieces of leather attached to one another with a metal stud. The leather band is then accented with metal flowers throughout…

$100.00
Available Colors:
  • NATURAL

…of packable polypropelene straw, the Craig Fedora is lightweight, packable (flexible) and water resistant. The Craig Fedora Hat is ideal for both men and women and is a great option for those looking for a hat with the look of straw, without the hassle straw hats require. What's not to love?  …

$65.00
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE

…leather hat band studded with metallic conch accents and distressed finish. The hat band doubles as an adjustable chincord that pokes through the brim; a branded Stetson "S" adorns the brim's left underside.    Great for both men and women, the new Comstock Straw Western Hat has the rugged…

$61.20
Available Colors:
  • NATURALBROWN

…  Boasting a classic western shape and aged finished, the Hollywood Straw Western Hat by Charlie 1 Horse is a stylish option for both men and women. Minimally adorned with a pattern-embossed and turquoise bead accented hat band, the Hollywood is finished with a flared, shapeable wire brim and…

$50.00

  Mayser Hats is a brand that is long associated with the highest levels of quality in hat making. A style for men, this lightweight straw fedora is designed with a high c-crown and an ultra stingy up-turned brim. A cotton tan band wraps around the crown and custom cotton sweatband lines…

$65.00
Available Colors:
  • TAN

  Made in Slovakia Mayser Hats is a brand that is long associated with the highest levels of quality in hat making. A style for men, this lightweight straw fedora is designed with a c-crown, contrasting white band and comfortable cotton sweatband to keep you cool when the…

$90.00
Available Colors:
  • BLACK

  Made in Mexico   The Fender Straw Cattleman Western Hat by Renegade features a squared-off cattleman crown and flared wide brim. Made of a stiff finish straw, the Fender is simple and classic. Ideal for both men and women, the Fender is a great way to top off your cowboy/cowgirl…

$50.00

…for both men and women, Boater or Skimmer hats were considered a warm weather must-have. Taking inspiration from this timeless classic, Brixton's Autumn Raffia Straw Boater Hat is designed specifically for women with a muted, yet feminine feel. Crafted of 100% natural raffia straw for a fresh…

$56.00
Available Colors:
  • CREAMBLACK
  • TAN
  • NAVYBLUE
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