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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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141 - 168 of 225 Products
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  Bailey's Foster Herringbone Plaid Wool Earflap Newsboy Cap is a 8/4 cap made of a wool blend. Convertible earflaps make this the perfect option for a cold and windy day. An attractive herringbone pattern with contrasting stripes are the stand out detail. The Foster is fully lined making for…

$76.50
Available Colors:
  • DENIMBLUE

  Please Note: This piece fits a little loose. Made in the USA Introducing the Dynamite Wool Felt Western Hat by Bailey. This cowboy hat is equiped with a DRI-LEX® sweatband to make sure that if you are getting a little hot, your hat isn't going to show proof of that…

(2)
$114.75
Available Colors:
  • BLACK

  Designed for those who thrive in the great outdoors and seek sun protection, Bailey's Dario Toyo Straw Blend Lifeguard Hat has an extra wide downturned brim perfect for keeping harmful rays off your face. The chin cord with adjustable toggle allows for extra security no matter the adventure.…

$100.00
Available Colors:
  • NATURAL

  Made in the USA   The 1890s slang word hightail originated from US cattle ranches, where many animals flee with their tail up. The Bailey Hightail Wool Felt Western Hat is made of a 2X wool felt firm/stiff body; it has a plaited cotton cord hat band, topped with a tricolor woven…

$127.50
Available Colors:
  • SILVERBELLY

  Made in the USA The Perry Lanolux Wool Felt Fedora Hat is crafted of 100% virgin wool with a luxurious sueded finish. Lanolux hats undergo an extra sanding process to create a lightweight and packable "Touch Me" finish for an unbelievably soft feel. Trimmed with a smooth leather…

(1)
$136.00

  Made in the USA   The Bailey Daxton Seagrass Straw Fedora Hat has arrived just in time for spring and summer! Featuring a lightweight and breathable seagrass straw build, the Daxton boasts a classic tear drop crown and slightly upturned brim. Details include a wide Japanese…

$170.00
Available Colors:
  • SEAGRASS

  Finished in the USA; Handwoven in Ecuador   The Phineas Two-Tone Panama Straw Fedora Hat is a new favorite from Bailey featuring genuine Panama straw which has been handwoven in Ecuador with leaves of toquilla palm. Its two-tone style is beautifully complimented by the Japanese…

$225.00

  Made in the USA   Introducing the Kilgore Raindura Toyo Straw Fedora Hat, part of the Bailey Wind River® collection of outdoor styles. The Kilgore is crafted in the USA using Bailey's exclusive Raindura finish that makes the straw both water resistant and shape retentive. The…

(1)
$138.00
Available Colors:
  • TAN

  Please Note: Due to the nature of the straw, there may be some variance from hat to hat and is part of its beauty and uniqueness.   Made in the USA   The Braylon Sisal LiteStraw Fedora Hat by Bailey features a finer weave than most other straws in a classic design,…

$170.00
Available Colors:
  • BLACK
  • NATURAL

  Made in the USA   Old fashioned style can be great, like the Chisolm Wool Litefelt Cattlemen Western Hat from the Wind River collection from Bailey. This classic western features a beautiful crushable/packable, water repellent wool felt body, with a comfortable padded DRI-LEX®…

(2)
$114.75
Available Colors:
  • BROWN

  Handwoven in Ecuador, Blocked & Finished in the USA   The Hurtle Panama Straw Fedora Hat is a unique piece by Bailey. Featuring a diamond crown that has been artfully ventilated, this genuine panama is headwear artistry at its finest. A Japanese grosgrain ribbon hat band and…

$225.00
Available Colors:
  • BLACK
  • TAWNY
  • LIGHTBLUE
  • NATURAL

  Made in the USA   The Bailey Darron Wool LiteFelt Pork Pie Hat is proudly made in the USA using their very own premium LiteFelt® finish for superior softness, flexibility, and repelling of water. Featuring the classic pork pie look including a telescope crown and stingy brim, the…

$130.00
Available Colors:
  • BLACK

  Made in the USA   Part of Bailey's Poet® Travel Collection, the Boley Wool LiteFelt Roll Up Fedora Hat weighs in at 4 ounces and rolls up for easy on-the-go storage. Made in the USA using Bailey's exclusive wool LiteFelt®, the Boley is soft, packable/rollable and water repellent,…

$110.50
Available Colors:
  • BLACK

  Bailey's Piston Wool Felt Aussie Hat is a staple for any hat aficionado's closet. A classic wide-brim aussie hat silhouette with a teardrop crown, this hat is completely crushable/packable. The Piston is designed with a vegan leather bolo cord with metal tips. Fully lined in cotton, this hat…

$68.00
Available Colors:
  • TAN

  Made in the USA   Make a statement with the Caprole Wool LiteFelt Walker Trilby Hat by Bailey 1922! The Caprole is a unique trilby that is water resistant, stain repellent, and shape retentive making it ideal for styling anywhere you go. It includes a removable side duck feather, a…

$123.25

  Made in the USA   Elaborate designs and bright colors were in vogue in the 1980's. This was a decade in which clothes became a major signifier for financial success and prosperity. Flash and flare were used to show that a person was part of the "better off" crowd. Billy Joel's tune…

(1)
$120.00
Available Colors:
  • PURPLE

  Made in the USA   The Bailey Darron Wool LiteFelt Pork Pie Hat is proudly made in the USA using their very own premium LiteFelt® finish for superior softness, flexibility, and repelling of water. Featuring the classic pork pie look including a telescope crown and stingy brim, the…

(5)
$130.00

  Made in the USA The Ore Raindura Straw Outback Hat, part of the Bailey's Wind River® collection of rugged outdoor styles, is crafted from a raindura straw blend and handwoven thermosetting yarn. This yarn makes the straw both water resistant and shape retentive. The Ore is made in…

$138.00
Available Colors:
  • ARMYGREEN
  • STONE

  It's all about the subtle details with the Ronit Toyo Straw Blend Trilby Fedora Hat by Bailey. The multi-colored braid adds dimension while the colorblocked grosgrain ribbon hat band adds contrast and interest. These finer details come together to a create a hat with effortless charm. …

$80.00
Available Colors:
  • NATURAL

  Bailey's Eli Two-Tone Vented Poly Braid Fedora Hat is a great hat for day excursions. Walk around town in this 2 1/2" brim dual colored braided fedora. The Eli features a grosgrain band with a color accent, and has a center dent that is flattering on all face shapes.    Approx. 4"…

(1)
$95.00

  Elevate your winter ensemble with the sleek Elbin Plaid Fabric Ivy Cap by Bailey 1922. Designed with comfort in mind, this plaid patterned flat cap is crafted from a rayon-poly blend, features a cotton sweatband, and is fully lined. The close-fitting design and contour flat shape ensures a…

$68.00
Available Colors:
  • CHARCOAL

  Handwoven in Ecuador; Finished in the USA   Multi-colored with a unique patterned weave, the new Giger Panama Straw Fedora Hat will take your breath away. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert Bailey craftsmen, the Giger's…

(1)
$215.00

  A tasteful and elegent ivy cap from Bailey, the Liam Linen Cotton Ivy Cap! Made of linen and cotton blend, this hat features a subtle windowpane plaid pattern. A new Bailey favorite, especially with the finishing touches of a cotton twill sweatband and fully lined interior.    …

$90.00
Available Colors:
  • BEIGE

  Handwoven in Ecuador; Finished in the USA   Caramel-hued and expertly crafted, the Tessier Panama Straw Fedora Hat by Bailey will add distinctive style to your look this spring and summer! Like all genuine panama hats, the Tessier's body was artfully handwoven in Ecuador then…

(2)
$220.00

  Handwoven in Ecuador; Blocked & Finished in the USA   The Keats Vented Panama Straw Fedora Hat combines artisanal handwoven Panama straw and the best of Bailey American craftsmanship in one stunning hat style. Starting with its handwoven body in striking colors, the Keats is…

$240.00

  Handwoven in Ecuador, Blocked & Finished in the USA   Bailey's Boreal Panama Straw Fedora Hat is a sight for eyes that want something new! With unique details like a twisted front dent tear drop crown and a two-tone body, the Boreal is sure to stun. Handwoven in Ecuador, this…

$225.00
Available Colors:
  • TAWNY
  • BLACK

  A new staple for any flat cap fan, the Liam Linen Cotton Ivy Cap by Bailey! Made of a soft cotton and linen blend, this hat features a stripe pattern. Features a sewn bill, Bailey side pin, cotton twill sweatband and cloth lining.   Approx. 9 1/2" Front to Back, Flat 9 1/2" Side to…

$90.00

  Get a new spin on a classic with the Ormond Wool Blend Ivy Cap from Bailey of Hollywood. This stylish cap features a unique offset paneled pattern adorning the crown, as well as a signature Bailey metal side pin on the back. The lined interior is comfortable, allowing for a great fit you'll…

$59.50
Available Colors:
  • BROWN

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