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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 (115)

Bailey Trilby Fedora

1 - 30 of 115 Products
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  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:
  • HUNTERGREEN

  Please Note: 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…

$83.00

…USA   Featuring their famous lightweight and water repellent 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…

$115.00
Available Colors:
  • NATURALBLUE

…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

  Made in the USA Introducing the Bailey Draper III Fur Felt Fedora Hat. For those that love their fur fedoras you can't go wrong with this piece and the gorgeous colors it comes in. The fur is a mix between rabbit and beaver and is soft to the touch.    Approx. 4 1/2"…

$325.00

  Introducing the Bailey Wilshire Toyo Braid Straw Fedora Hat with the gorgeous collection of colors to grab your eye and the lovely rounded teardrop crown will make this hat your new favorite everyday hat.   Approx. 4" Rounded Teardrop Crown 2" Snap Brim   Made of: 50% Toyo…

$70.00
Available Colors:
  • COPPER
  • BLACK
  • NAVYBLUE
  • SAND

…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

…town.    A matching braided band and loop with the Bailey logo nicely finishes off the outside, while a comfy custom Bailey sweatband should keep you comfortable for every event, day or night. The Bailey of Hollywood Billy fedora is a casual masterstroke from a true quality brand. …

$60.00

  UPF 50+   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…

$68.00

…Lichter 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…

$70.00

…color 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…

$70.00
Available Colors:
  • CHARCOAL

  The new Rokit Toyo Straw 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…

$65.00

  Introducing 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…

$70.00

  Crafted of their exclusive 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…

$70.00

  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

  Made in the USA   With a stingy brim and overall smaller profile, the Goldring 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…

$88.00
Available Colors:
  • NAVYBLUE
  • SILVERBELLY

  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

  Part of 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.…

$90.00

…USA The dapper Yates Wool LiteFelt 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…

$81.00
Available Colors:
  • BLACK
  • PEWTER

  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…

$70.00
Available Colors:
  • FORESTGREEN

…the Tor Short Panama Straw Trilby Fedora Hat by Bailey is a new style for spring and summer featuring a custom contrasting weave. Handwoven by artisans in Ecuador, the Tor Short Trilby is blocked into its sleek shape and finished with deluxe details at the Bailey factory in the USA. A center…

$175.00
Available Colors:
  • NATURALBLACK

  Made in the USA   Featuring Bailey's signature wool lite felt, the Chipman Wool LiteFelt Trilby Fedora Hat featueres their lightweight, soft and packable LiteFelt® finish with the added benefit of natural water repellency. Part of Bailey's Breed collection which seeks to celebrate…

$85.50

  Please Note: 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…

$83.00

…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%) furs with a stouter crown and shorter brim when compared to their original Duffy Fedora style. A narrow grosgrain ribbon hat band, micro Bailey staple side…

$325.00
Available Colors:
  • CAMEL

… The Bailey New Yorker Fedora is a classic, center dent fedora that spans decades of hat fashion. Approx. 4" Center dent Crown Approx. 1 7/8" Snap Brim Made of: 100% Wool Custom Bailey Lining Cotton Sweatband Wide Grosgrain Headband Prong Back Oval Bailey Pin Removable…

$95.00

  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

…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

  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

…protection for the sun - and he still needed to look good doing it.   Approx. 4" Teardrop Crown 2 3/8" Brim Made of: 100% Genuine Panama Straw (Cuenca Weave)   Grosgrain Ribbon Hat Band Bailey Side Pin Woven Polyester Sweatband   Sizes: S, M, L, XL and XXL  

$140.00

  Made 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…

$105.00

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