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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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…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

…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…

$88.00
Available Colors:
  • NATURAL

  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…

$64.00
Available Colors:
  • BROWN

  Be Bold. Take a chance. Be a Gambler.   Something Special Untrimmed Toyo Straw Gambler Hat does not get any less bold than this. This hat will give an air of confidence. You won’t be missed in the Untrimmed Gambler.   Approx. 3 3/4" Telescope Crown 3 1/2" Brim   …

$18.95
Available Colors:
  • GOLD
  • SILVER

  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"…

$45.00
Available Colors:
  • BLACK

…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

…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…

$120.00
Available Colors:
  • NATURAL

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

$49.00
Available Colors:
  • IVORY

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

$115.00
Available Colors:
  • DARKNATURAL
  • NATURAL

  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

…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 tan Panama Hat will keep…

$85.00
Available Colors:
  • TAN

…course with the Vent Crown Toyo Straw Gambler Hat by Scala! Featuring a classic telescope crown, the Vent Crown Gambler ups the ante with stylish and perfectly breathable vents woven along the crown's sides. A classic 3-pleat cotton twill hat band adorns the hat and is finished with an oval Scala…

$58.00
Available Colors:
  • IVORY

…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
Available Colors:
  • NATURAL

  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.…

$165.00
Available Colors:
  • NATURALOLIVE

…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

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

…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 the entire band. Simply Gorgeous.   Approx. 4" Gambler

$100.00
Available Colors:
  • NATURAL

Hat, part of the Stetson Crushable Western Collection. The Black Hawk serves a gambler style 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

$67.50
Available Colors:
  • BLACK

New Era Otis Pork Pie is fashioned after a classic among men's hats. The Pork Pie hat has a long history replete with long, sweaty Jazz sessions in speakeasy full of liquor and cigarette smoke. This hat is an icon, so when wearing it wear it with pride. Approx. 3 3/4" telescope crown Approx. 1…

$48.00
Available Colors:
  • BLACK

…Jett Porkpie combines a classic men's style, with Bailey's fashion forward Jett Nap Finish. These premium wool felts are crafted with Bailey's exclusive blend of 100% virgin wool fibers and a unique silk-like finish, adding a luxurious sense and character. The hat comes fully lined in satin. 4"…

$100.00
Available Colors:
  • BLACK

…size above your normal size.  Soft, luxurious, warm, all faux fur trapper hats in Black have arrived from Jaxon Hats. This is the classic Trapper hat, made of 100% acrylic with a comfy padded lining. For men and women. Approx. 6 1/2" long earflaps. Made of: 100% acrylic - faux…

$12.00

Stacy Adams...for Men of Distinction. Keeping with Stacy Adam's tradition of bringing the finest in men's headwear, we bring you the same exceptional quality and fashion detail that you have come to expect from the 140 year old company, with the Pinch Homburg Hat. Taking the classic homburg shape,…

$58.00
Available Colors:
  • BROWN

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?    Approx. 3 7/8" Pinch Crown 2" - 2 1/8" Snap Brim   Made of: 100% Polypropelene   Grosgrain Hat

$65.00
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE
  • RED

…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 makes this style both packable/crushable and water repellent. No stiff hats

$68.00
Available Colors:
  • BLACK

  Introducing the Helen Kaminski XY for men Abaka Fedora hat. This piece is made with natural fibres so it is able to breathe and is cool to wear. It is also flexible and the raffia prevents brittleness. If you are a little more rough with your hats this is a great piece for you.   …

$220.00
Available Colors:
  • BROWN
  • STORM

  Warm and soft, the new Geo Knit Beanie Hat by Woolrich is a stylish new beanie for fall and winter. Featuring a stylish geometric-inspired, two-tone knit design, this beanie has a double-wall construction for extra warmth. Great for both men and women, this style adds a bit of flair to your fall…

$8.00
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