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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 (101)

Bailey Fedora Hats

1 - 30 of 101 Products
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…fine toyolene braid, Bailey's Hooper Toyo Straw Blend Trilby Fedora Hat is not only incredibly breathable but also completely packable and crushable. Hooper features a color-blocked braided weave blocked into a tear drop crown and all-around snap stingy brim. A striped inlaid "hat band" adorns the…

$70.00

…Billy fedora is a casual masterstroke from a true quality brand.   Approx. 3 7/8" Crown 1 3/4" Brim   Made of: 55% Toyo Straw 45% Polyester    Self Hat Band Cotton Sweatband Bailey Side Pin OR Tag Unlined    *Due to different shipments from Bailey, hats

$51.00

  Made in the USA The Bailey Silko Wool Felt Trilby Fedora Hat is a style that everyone needs in their wardrobe.  The distinctive diamond crown with the diamond pattern perforations makes this hat very unique.   Approx. 3 3/8" Diamond Crown 1 1/2" Snap Brim   …

$90.00
Available Colors:
  • BLACK
  • HUNTERGREEN

…The Gysin Teardrop Fedora Hat by Bailey features a natural horse hair hat band and a supple goatskin leather sweatband. Made from 100% wool felt with a proprietary Doeskin stiffened finish, the Gysin Teardrop Fedora Hat is a stylish cross between traditional dress hat and a western. A showcase…

$170.00
Available Colors:
  • BLACK
  • CHINO

…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…

$70.00
Available Colors:
  • CHARCOAL

…Breed® line of hat styles, the Romeo Raffia Straw Blend Trilby Fedora Hat by Bailey is a fresh and contemporary straw style for spring and summer. Crafted of an exclusive raffia and polyester blended braid, Romeo boasts a soft and pliable finish not usually found in straw hats. Its loose weave is…

$90.00

…Wool LiteFelt Trilby Fedora Hat by Bailey is a handsome new style for fall and winter. The Goldring is crafted in the USA of premium wool LiteFelt® for a soft, packable/crushable and water repellent finish. Its classic pinch crown is adorned with a striped grosgrain ribbon hat band with a fold-over…

$88.00
Available Colors:
  • NAVYBLUE
  • SILVERBELLY

…This style no longer ships with a Bailey side pin. Instead, this style now has a small printed Bailey logo on the side bow.    Made in the USA The Tino Wool Felt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines traditional craftsmanship…

$70.55

…Foregoing traditional hat bands and side feathers, Chipman is unlined and accented with a simple Bailey staple pin at its back. Wear the crown as is for a homburg/godfather-inspired look or pinch in the front sides of the crown for a classic fedora hat look â the Bailey Chipman easily compliments…

$95.00

…Trilby Fedora Hat by Bailey is a wonderful addition to their masculine Poet® collection. This packable and water repellent fedora has a stingy rolled brim that pre-snapped at the front for a classic fedora look with a smaller overall profile. Its smooth leather hat band accents the hat nicely while…

$90.00
Available Colors:
  • BLACK
  • PEWTER

…Made in the USA   Bailey's new Horton Polished Wool Felt Trilby Fedora Hat features a luxurious polished wool finish for added texture and sheen. With its center dent crown and stingy brim, Horton boasts an overall smaller profile than traditional fedoras for a more trilby-like design.…

$125.00
Available Colors:
  • MINK

…the Bailey of Hollywood Vito Toyo Straw Braid Trilby Fedora Hat which has a great combination of colors. The pattern on the crown creates the appearance of a hat band without one actually being present. This hat is also crushable so you don't have to worry about someone picking up the hat and…

$59.50

…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

$70.00

  Made in the USA   The new Bailey Craven Wool LiteFelt Trilby Fedora Hat has a modern and stylish look you want with the functionality you need. Featuring Bailey's premier wool LiteFelt® finish, the Craven is soft, packable and water repellent with the added benefit of a flannel…

$105.00

…a wide Japanese grosgrain ribbon hat band and small Bailey staple side pin; its super short (i.e. stingy) brim is upturned for maximum effect. One of a kind design in a stylish and modern shape, the Tor Short Panama Straw Trilby Fedora Hat is a genuine panama hat with contemporary flair.  …

$175.00
Available Colors:
  • BLACKNATURAL
  • NATURALBLACK

…thermo, the Bailey Elliot Straw Fedora Hat offers a breezy option for spring and summer. Lightweight and stylish, the Elliot features a pinch front crown, narrow grosgrain ribbon hat band and a stingy, pre-snapped brim. Don't sweat it this spring/summer, just wear your Elliot Fedora and enjoy the…

$51.00
Available Colors:
  • NATURAL
  • NAVYBLUE

  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…

$55.25
Available Colors:
  • TANBROWN

  Made in the USA   Bailey Hat's most popular fedora. This premium wool felt is created with their exclusive blend of 100% virgin wool fibers, specially finished by their skilled craftsmen resulting in superior quality and unequaled value.   Approx. 4" crown 2 1/2" snap…

$80.75
Available Colors:
  • BLACK

…LiteStraw® finish, the Creel Shantung LiteStraw Fedora Hat by Bailey gives the classic warm-weather straw fedora hat a stylish twist. Crafted with a timeless pinch front crown and 2.5-inch wide brim, Creel is smartly trimmed with a navy and grey striped hat band with side bow for a unique, summery…

$115.00
Available Colors:
  • NATURALBLUE

  Made in the USA   Bailey's Est. 1922 hats feature updated, contemporary versions of their timeless archived designs. The new Duffy II Superior Fur Felt Trilby Fedora Hat is crafted in the USA using Bailey's superior fur felt blend consisting of premium beaver (40%) and rabbit…

$325.00
Available Colors:
  • CAMEL

  Bailey introduces the Fernales Fedora that brings that classic style with you from your fall/winter hat into spring/summer style.   Aprrox. 4" Crown 1 3/4" Pre-Snap Brim   Made of: 100% Palm Straw   Unlined Bailey side pin Grosgrain ribbon band   …

$51.00
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 hat band.…

$70.00
Available Colors:
  • FORESTGREEN

…style no longer ships with a Bailey side pin. Instead, this style now has a small printed Bailey logo on the side bow.    Made in the USA The Tino Wool Felt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines traditional craftsmanship…

$70.55

Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish gives the hat its soft and packable nature in addition to adding water repellency. Good looks and functionality can coexist! Bailey's Blixen Wool LiteFelt Fedora Hat has…

$74.80

  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

…in the USA   The Bailey Sturges Wool LiteFelt Fedora Hat is crafted in the USA using Bailey's exclusive wool LiteFelt® finish that gives the Sturges its soft and packable feel as well as its water repellent properties. Trimmed with a braided waxed cord hat band, Sturges is finished with…

$105.00

…striped hat band gives Bailey's Tharp Shantung LiteStraw Fedora Hat a singularly striking spring/summer feel. Proudly crafted in the USA using their exclusive LiteStraw® finish, the Tharp is a soft, lightweight and water repellent straw hat blocked into a stylish tear drop crown fedora style. Its…

$115.00
Available Colors:
  • NATURALBLUE

…being water repellent. Its stingy-brimmed fedora 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…

$63.75

…  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!   Approx.…

$215.00
Available Colors:
  • NATURAL

…Fur Felt Fedora Hat has a crown you don't see every day. This piece is a great hat to add to your collection because it is unique and is made to perfection.   Approx. 4" Crown 2 3/4" Brim   Made of: 100% Fur Felt   Made in the USA Grosgrain Hat Band Bailey Side Pin…

$350.00

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