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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 (87)

Bailey Trilby Fedora

1 - 28 of 87 Products
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  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…

(3)
$78.00

Bailey Mannesroe fedora that adds a little color and style to your life. It is a great hat to spend the day walking around town in without feeling over heated.   Approx. 4" Center Pinch Crown 2" Snap Brim   Made of: 100% Polypropylene   Comfort Sweatband Unlined Bailey

(1)
$66.00

…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…

$52.50
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…

(1)
$72.00

…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

(1)
$52.50
Available Colors:
  • BARK

  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

…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…

$95.00
Available Colors:
  • BLACK

  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.…

$100.00
Available Colors:
  • NATURAL

  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…

$125.00
Available Colors:
  • HONEY
  • SILVER
  • NATURAL

  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…

(11)
$100.00

…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.    Village Hat Shop Exclusive Colors   Made in the USA The Tino Wool Felt Trilby Fedora Hat from Bailey is a great looking hat at a great…

(1)
$100.00

  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

  Get ready for summer with the Freddy Braid Fedora Hat from Bailey! This packable, crushable hat is perfect for travel, and features alightweight  breathable unlined interior with a cotton twill sweatband. Best of all, the heathered build is incredibly comfortable!   Approx. 4"…

$75.00
Available Colors:
  • BLACK
  • RUST
  • BLUE

  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…

(4)
$120.00
Available Colors:
  • BLACK

  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…

$75.00
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE
  • RED

…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…

$65.00
Available Colors:
  • NATURAL
  • NAVYBLUE

…Teardrop Crown 2 3/8" Brim Made of: 100% Genuine Panama Straw (Cuenca Weave)   Handwoven in Ecuador Blocked & Finished in the USA Double Layer Japanese Grosgrain Ribbon Hat Band Bailey Side Pin Fine Woven Sweatband   Sizes: S, M, L, XL, and XXL; fits true to size.  

$155.00

  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.  …

$48.75
Available Colors:
  • TANBROWN

…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

…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 quality!   Approx. 3 1/2" Pinched Crown…

$175.00
Available Colors:
  • NATURAL

  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

  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 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. …

$160.00
Available Colors:
  • NATURAL

…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…

$75.00

…the 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…

$170.00
Available Colors:
  • NATURAL

…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…

(1)
$135.00
Available Colors:
  • NATURALBLUE

  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…

$145.00
Available Colors:
  • NATURAL

…The Bailey of Hollywood Sydney Panama Straw Fedora Hat owns the summer with a strong straw weave that should stand the test of several Summers. Undeterred by the season's bright sun and general wear and tear, quality and style are heavily featured in this stingy brim genuine Panama fedora.

$150.00
Available Colors:
  • NATURAL

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