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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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  • Retail (93)

Bailey Fadoras

1 - 28 of 93 Products
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  Made in the USA Introducing Bailey's Konrath Shantung LiteStraw Fedora Hat. This is a gorgeous straw fedora crafted of premium shantung straw and boasts Bailey's exclusive LiteStraw® for a lightweight, supple and water resistant finish. You can't go wrong with this piece. …

$150.00
Available Colors:
  • NATURAL

  Made in the USA The Curtis Wool Felt Safari Fedora Hat is one of the most practical hats in the Bailey line. The classically designed safari fedora repels water and oil based spills. It is breathable, and durable and can be packed for ease of travel.    Approx. 4" Center…

(3)
$98.00

…100% Shantung LiteStraw®    Made in the USA Exclusive LiteStraw® Finish - Lightweight & Water Repellent Navy & gray Striped Hat Band w/ Side Bow Bailey Side Pin DRI-LEX® Absorbent Sweatband Bailey Crown Tip Inner Label   Sizes: S, M, L, and XL; fits true to size.  

(1)
$135.00
Available Colors:
  • NATURALBLUE

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey of Hollywood Blixen Midnight Blue Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt®…

$98.00

  You're comfortable and cool-looking when you're wearing the Stanley Fedora Hat from Bailey. This well-made fedora features a stiffened, dyed braid, a matching woven hat band with a Bailey metal side pin, and a comfortable cotton twill sweatband. If you want to turn heads, this hat is one…

$80.00
Available Colors:
  • DARKNATURAL

…outdoorsman crown -  a mix between traditional pinch and teardrop crowns - the Lapkus Wool Felt Fedora Hat by Bailey is an eye catcher. Finished with a Japanese grosgrain ribbon hatband, small Bailey side pin and cotton sweatband - the Lapkus is also both packable and water repellent.    …

$90.00
Available Colors:
  • COGNAC

  Introducing the Bailey Tennessee Fedora Hat. This is a great lightweight summer hat to keep you cool and protected from the sun at the same time. The brim and the crown are two different colors but the plaid hat band make them sync perfectly together. You can't go wrong with this piece.  …

$48.75
Available Colors:
  • TANBROWN

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey of Hollywood Blixen Camel Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish…

$98.00
Available Colors:
  • CAMEL

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey of Hollywood Blixen Dark Green Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt®…

$98.00
Available Colors:
  • DARKGREEN

  Made in the USA   The new Bankhead Wool Felt Fedora Hat by Bailey features their exclusive 606 Finish for a luxurious sheen and feel. Crafted of the finest 16-micron wool, felts destined for the premier 606 finish are blended, double carded, and hand wet felted. Afterwards, a light…

$81.00

  Made in the USA   Bailey's Browtine Wool LiteFelt Safari Fedora Hat is part of their rugged Wind River® Collection of hats. The Browtine is crafted in the USA using Bailey's exclusive wool LiteFelt® finishing process to create a hat that is lightweight, packable, crushable and water…

$72.00
Available Colors:
  • SERPENT

  Made in the USA   The Harvey Shantung Straw Fedora Hat by Bailey offers a quirky and singular style not often seen in fedoras. The Harvey Fedora is crafted of firm shantung straw and boasts an intricate vent woven crown (sides). Its wide brim is offset with a twisted, reversible…

$140.00
Available Colors:
  • NATURAL

  Introducing the Tavion Abaca Straw Braid Fedora Hat by Bailey. This is a great lightweight hat that is comfortable and won't weigh you don't. THe hat band is created as one with the hat to create one solid piece.   Approx. 4" Crown 2 3/4" Brim   Made Of: 100% Abaca…

$75.00
Available Colors:
  • NATURAL

…blocked design, the Grimet Toyo Braid Straw Trilby Fedora Hat by Bailey is an eye-catching, sleek style. Crafted of extra fine braided Toyo straw for a lightweight and packable finish, Grimet keeps the details simple with only a small Bailey staple side pin. Its stingy snap brim can be worn snapped…

$52.50
Available Colors:
  • CHARCOAL

  The Marr Wool Fedora Hat from Bailey of Hollywood is sure to become a staple of any wardrobe. The colorful grosgrain hat band is incredibly sophisticated, with the lined interior and heavy sweatband make for a most comfortable fit. Add it to your wardrobe today!   Approx. 4" Pinched…

$45.00
Available Colors:
  • OLIVEGREEN

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey of Hollywood Blixen Lapis Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish…

$98.00

…Village Hat Shop Exclusive Color   Made in the USA   Introducing the new Packable Wool LiteFelt Fedora Hat by Bailey! Part of their Bailey by Hollywood classic men's line, the new Packable Fedora is exclusively sold at the Village Hat Shop and features their premium LiteFelt®…

$98.00

…  Bailey's unique Larsen Leather & Sisal Straw Fedora Hat boasts a singular design that combines lightweight sisal straw with smooth overlaid genuine leather. Crafted by expert Bailey craftsmen in the USA, the Larsen is simply breathtaking. A tonal side feather and Bailey staple pin…

$225.00
Available Colors:
  • NATURALBLACK

…best, like the Stansfield Panama Straw Fedora Hat from Bailey! This American-made hat is made of fine, reliable panama (toquila palm) straw, complete with a leather hat band and woven detail wrapping around the crown. Quality matters, and Bailey knows that!   Approx. 3 3/4" Teardrop Crown…

$160.00
Available Colors:
  • NATURAL

…the USA   Introducing the Bailey Roll Up II Panama Straw Fedora Hat that can be rolled and placed into a bag for traveling. It is lightweight, comfortable and an all-around great find. Get the traditional Optimo crown Panama hat look with the Bailey Roll Up II Panama Fedora Hat! …

$215.00
Available Colors:
  • NATURAL

…design boasts a classic pinch front crown with grosgrain ribbon trim and small Bailey staple side pin. Enjoy the best of both style and function with the smart-looking Lando Toyo LiteStraw Fedora Hat by Bailey!   Approx. 3 3/4" Pinch Front Crown 2" Snap Brim   Made of: 100%…

$75.00

…USA   The Cutler is a most excellent and stylish Cuenca weave Panama. This beauty from Bailey is the perfect casual summer fedora. It comes complete with a stunning leather band and Bailey hat pin.     Approx. 4" Center Pinch Crown 2 7/8" Pre-snap Brim   Made of: 100%…

(4)
$155.00
Available Colors:
  • NATURAL

…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 Kilgore…

$88.00
Available Colors:
  • TAN

  Made in the USA   The Anderson Shantung LiteStraw Fedora Hat boasts Bailey's exclusive LiteStraw® finish for a supple feel and added water repellency. Enjoy the handsome look of the Anderson without the stiffness or extensive care of other straw hats. The Anderson features a center…

$120.00
Available Colors:
  • NATURAL

…two-toned geometric weave, the new Arsun Two-Tone Straw Fedora Hat by Bailey steals the show. The Arsun boasts a classic pinch front crown and mid-width brim combined with a simple grosgrain ribbon hat band and Bailey micro-staple side pin. Stylized venting woven along the crown's circumference…

$145.00
Available Colors:
  • BLACKWHITE

  Handwoven in Ecuador, Finished in the USA   Quality matters, like with the Parson Panama Straw Fedora Hat from Bailey. This fine hat features a narrow cotton herringbone hat band, as well as a contrast color bound edge around the brim. This USA-made fedora is of the highest…

$170.00
Available Colors:
  • NATURAL

  Featuring Bailey's exclusive Winter Toyolene Braid, the new Ragon Toyo Braid Straw Trilby Fedora Hat features a sleek and modern design with an almost-clothlike feel and finish. Ragon features a trilby fedora design with an overall smaller profile, a color-blocked finish and no traditional…

$52.50
Available Colors:
  • FORESTGREEN

…braid, Bailey's Truro Toyo Straw Blend Trilby Fedora Hat is not only incredibly breathable but also completely packable and crushable. Truro features a pliable braided chevron weave blocked into a classic pinch front crown and all-around snap stingy brim. A striped inlaid "hat band" and Bailey

(1)
$52.50
Available Colors:
  • BARK

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