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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 (116)

Bailey Fedora Hats

1 - 30 of 116 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

  Please Note: Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band. Welcome to today's hot new look in an amazingly soft, packable, and comfortable sewn braid! The Bailey of Hollywood Billy is a top selling topper with a stingy…

$60.00

…  The Bailey Toyo Straw Fedora Hat is part of ále by Alessandra's new line for spring and summer. Featuring a classic fedora design adorned with a paisley bandana hat band, the Bailey has a unique look perfect for casual wear. Rest easy knowing you are protected not only by the hat's wide brim…

$68.00

  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   Made…

$81.00
Available Colors:
  • BLACK
  • HUNTERGREEN

…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

…Braid Trilby Fedora Hat by Bailey is great-looking, packable/crushable and lightweight. Its stylish color-blocked two-tone design gives this hat a unique look while its coordinating striped hat band adds style. The Rockit can be dressed up or down, making it a versatile and handsome hat to have in…

$65.00
Available Colors:
  • NATURAL

…Toyo Straw Trilby Fedora Hat by Bailey features a striped design in a classic trilby fedora shape. Crafted of their famous toyo straw braid, the Lichter boasts a stiffer finish than their famous Billy and other similar styles. A self-straw hat band adorns the crown; a Bailey micro staple side pin…

$70.00

…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:
  • CHINO

  Made in the USA   The Cosmo Toyo LiteStraw Trilby Fedora Hat by Bailey features a finer weave than most other toyo straws in a classic and lightweight design perfect for spring and summer. Made in the USA with Bailey's famous LiteStraw® finish, the Cosmo is lightweight, flexible and…

$120.00
Available Colors:
  • HONEY
  • SILVER

…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…

$90.00
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…

$83.00

…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 — the Bailey Chipman easily compliments…

$85.50

…their 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…

$90.00

…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…

$81.00
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…

$70.00

…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

  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.  …

$65.00
Available Colors:
  • TANBROWN

  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

…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…

$60.00
Available Colors:
  • NATURAL
  • NAVYBLUE

  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…

$95.00
Available Colors:
  • BLACK
  • CORDOVABROWN

  Bailey introduces the Craig Straw Fedora Hat, a new straw fedora for the spring and summer season. Crafted of packable polypropelene straw, the Craig Fedora is lightweight, packable (flexible) and water resistant. The Craig Fedora Hat is ideal for both men and women and is a great option for…

$65.00
Available Colors:
  • NATURAL
  • RED

  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

…braided waxed cord hat band, Sturges is finished with a Bailey-branded leather closure, an underwelt brim and adjustable sweatband. Take on the outdoors with confidence while wearing your handsome and functional Sturges LiteFelt Fedora, part of Bailey's rugged Poet® collection of hats.    …

$105.00

…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 (60%)…

$325.00
Available Colors:
  • CAMEL

…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…

$88.00

…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

…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 fold overlay hat band, side bow, side…

$120.00
Available Colors:
  • NATURAL

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