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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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Bolero Or Gaucho Hat

1 - 28 of 2510 Products
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…Felt Gaucho Hat by Bigalli. Made in Ecuador with 100% wool felt, this water repellent hat showcases both incredible craftsmanship and versatile functionality. Featuring an optimo crown and stiff raw edge flat brim, key characteristics of the gaucho style. Trimmed with a grosgrain ribbon hat band and…

$69.95
Available Colors:
  • BLACK
  • BERRY

…Bohemian Toyo Straw Gaucho Hat from Biltmore is undeniably high quality! This wonderful hat features a grosgrain ribbon hat band wrapping around the crown, paired with thin faux leather braiding. Additionally, the soft sweatband is so comfortable, you'll never want to take this hat off!   …

$100.00
Available Colors:
  • BLACK

…or call us at 1-888-847-4287 for help with sizing. XS = 6 3/4 S = 7 M = 7 1/4 L = 7 1/2   The Vale Wool Felt Gaucho Hat from Brixton Hats is a traditional hat shape found amongst the plains of Patagonia. The linear design has a firm/stiff body, built for long wear and tear. The simple…

$109.00
Available Colors:
  • COFFEE

  Jaxon Hats' newest leather hat, the Crusher Leather Outback Hat, is made of 100% genuine leather with a gorgeous polished finish. This hat is all about being sleek, from the braided leather hat band to the semi-circle leather sweatband. If your looking for a hat that's a little bit different…

(1)
$79.95
Available Colors:
  • BROWN
  • BLACK

…in the USA Trivia question: Name a hat worn by Spanish dancers and cowboys from Argentina. Hint: Also worn by “The Curse of Capistrano”.   The Bolero, of course! Also called a Gaucho hat, this was originally a working hat worn on the plains of Patagonia. Plain or embroidered…

(30)
$79.95
Available Colors:
  • BLACK

  What do you take on your pizza? Topped with the works, Jacobson's Pizza Hat is deliciously pie-tastic! Wear it on National Pizza Day, February 9th, or just because! Who doesn't love pizza? As seen in the film, "Everything Everywhere All at Once".   Approx. 14” Diameter   …

(1)
$14.95
Available Colors:
  • MULTI

…testament of their dedication to their culture and history. You can own a piece of artwork that that happens to be a hat, with the beautiful Cordoban Panama Straw Bolero Hat.   Approx. 3 3/4" Flat Top Crown 3 5/8" Downturned Brim   Made of: 100% Genuine Panama Straw   …

$132.56
Available Colors:
  • BLACKNATURAL

Gaucho Hat from the Toucan Collection, conjures up images of artistic Santa Fe, New Mexico. The wide brim gaucho style makes one think of the wild west, while the colorful multi-material hat band ties back to the famous artisanal handicrafts of the Southwest. The Turquoise Band Toyo Straw Gaucho Hat

$78.00
Available Colors:
  • NATURAL
  • BLACK

…option, then look now further than the Toucan Collection's Vegan Wool Felt Gaucho Hat. Finished to appear as if it's made of wool felt, this hat is actually completely vegan. In the oh-so popular gaucho design, this hat is fashion without the price tag! A must for your fall/winter wardrobe. …

$56.00
Available Colors:
  • SAND

  The Scala Hank Wool Felt Gaucho Hat is a handsome silhouette, a style inspired by the iconic hat worn in the great South American grasslands since the mid-18th century. The broad brim compliments the telescope crown, creating a layered linear look that garners attention. Get ready for the…

(2)
$85.00
Available Colors:
  • CHOCOLATEBROWN

…or call us at 1-888-847-4287 for help with sizing. XS = 6 3/4 S = 7 M = 7 1/4 L = 7 1/2   The Vale Wool Felt Gaucho Hat from Brixton Hats is a traditional hat shape found amongst the plains of Patagonia. The linear design has a firm/stiff body, built for long wear and tear. The simple…

$98.10
Available Colors:
  • BEIGE
  • BLACK

…sizing.  S = M M = L L = XL XL = XXL XXL = XXXL   The Jaxon Wool Homburg Hat is a classic! Once more popular than the fedora throughout Europe and America, this classic style was considered as formal as top hat and derby styles. Later nicknamed the "Godfather" by popular American culture,…

(29)
$59.95
Available Colors:
  • BLACK

  Stacy Adams Wool Felt Derby Hat is a hat for the customers that aren't a fan of the crushable hats. This piece is stiff and will stay to its original form if you take care of it. The lining in this hat is gorgeous and makes this piece a true classic.   Approx. 4 1/2" Round Crown  2"…

(2)
$85.00
Available Colors:
  • IVORY
  • BLACK

…Ciao Bella Wool Felt Gaucho Hat. One cannot help but notice the wide brim that surrounds the expertly blocked telescope crown. Hello beautiful!!   Approx. 3 7/8" Telescope Crown 3 1/2" Brim   Made of: 100% Wool Felt   Firm Felt Grosgrain Ribbon Hat Band Raw Edge Brim…

$78.99

…3 Regions Trade Co. Brisa Grade 4-5 Panama Straw Gaucho Hat pays homage to the gaucho, the "cowboys" of South America. Skilled horsemen, experts in traditional livestock farming, need the right gear and the 3 Regions Trade Co. Brisa Gaucho Hat fits the bill. The broad brim ensures the sun's glare…

$132.56

…available from Elope, the Narwhal Hat makes the "Unicorn of the Ocean" into a fun hat! Featuring a soft faux fur finish, the Narwhal Hat sports light blue spots on the top of its head and a metallic soft horn. Perfect for both children and adults, the Narwhal Hat is an adorable new topper that's…

$24.95

  This authentic hand-pressed Derby Hat (aka Bowler) is made of faux ultra-suede and features a distressed polyester band. Perfect for Victorian-inspired costumes or as the crowning finish to your steampunk costume.    Approx. 5 1/2" Round Crown 2" Curled Brim   Made of:…

(23)
$24.95
Available Colors:
  • BROWN
  • BLACK

…in Mexico   The classic bolero/gaucho style hat is now available in genuine Mexican palm leaf straw ideal for spring and summer! Charlie 1 Horse presents their Vaquera Palm Leaf Straw Bolero Hat featuring a handsome studded suede hat band and their famous branded horseshoe logo. Its wide…

$89.95
Available Colors:
  • COPPER

…tag of this hat reads S/M. Since only this size is available on our website, we have decided to label this hat as one size fits most. For more specifics on the sizing, please see the sizing notes in the description below.   Made in Ecuador   The Eve Wool Felt Bolero Hat is a true…

(1)
$100.00
Available Colors:
  • CREAM
  • KHAKI

  UPF 50+ Sun Protection   The Mercedes Wool Felt Gaucho Hat by Scala is an elevated version of the workwear classic. The tonal grosgrain ribbon hat band intertwines with the crown via grommets, creating a streamlined and unique look.   Approx. 3 1/2" Telescope Crown 3 3/4"…

(1)
$72.00
Available Colors:
  • BLACK
  • RUST

…the a luxurious wool felt finish. The Lang Elite Wool Felt Gambler Hat is then treated with a 'hand-cooked' shellac for the heritage stiffened touch. No detail has been overlooked on the Bailey 1922 Lang Elite Wool Felt Gambler Hat.   Approx. 4 1/4" Teardrop Crown 3" Snap Brim   …

$187.00
Available Colors:
  • BLACK
  • DENIMBLUE
  • ARMYGREEN

hat band that pulls through the brim and ties around your chin to provide additional protection against the wind. Traditionally worn throughout Southern America in cattle work, the Gaucho or Bolero style's main draw is their stiff wide brim that keeps the sun out of your eyes.  Looking for a hat

(1)
$185.00
Available Colors:
  • BLACK

…Crushable Outback by Jaxon Hats offers the perfect compromise between a fedora and western hat. A teardrop crown is sleekly embellished with a smooth composite leather hat band while its generous brim curves at both the front and back. Made of soft 100% wool felt, the Jaxon Hats Crushable Outback is…

(238)
$59.95
Available Colors:
  • BLACK
  • BROWN
  • PECAN

…Wool Felt Cowboy Hat by Jaxon features a bonafide western look with both good looks AND functionality. Its timeless c-crown (aka teardrop crown) is adorned with a smooth faux leather hat band complete with classic stud conch embellishments and side tails. A small Jaxon Hats 'J' side pin and stylish…

(14)
$59.95
Available Colors:
  • BLACK

  New from Biltmore Vintage Couture, the Styles Toyo Straw Gaucho Hat! This gaucho features an ultra stiff body and telescope crown. Wrapped around the crown we have a leather hat band and chin cord. The final touch, a feather accent piece!   Approx. 4" Telescope Crown 3 1/2" Flat…

$99.00
Available Colors:
  • BLEACH

…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 metallic concho accents add flair and…

(4)
$59.95
Available Colors:
  • BLACK

  New for Fall, the Firrella Knit Wool Blend Gaucho Hat by Scala! This knitted beauty comes to us with a knit wool blend, wax cord hat band and a drawstring sweatband. The best part, its flexible for your convenience   Approx. 3 1/2" Telescope Crown 3 1/4" Floppy Brim   Made…

$40.00
Available Colors:
  • BLACK
  • PECAN

  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"…

(21)
$59.95
Available Colors:
  • BLACK

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