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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 (121)

Bailey Trilby

1 - 28 of 121 Products
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…luxurious Bailey custom woven polyester sweatband that conforms to your brow, inasmuch as your look conforms to anything but your own fashion standards.     Approx. 3 1/2" Teardrop Crown 1 5/8" Snap Brim   Made of: 100% Polypropylene Braid   Black Bailey Side Pin…

$66.00
Available Colors:
  • WINE

  Combining toyo straw and 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…

$65.00
Available Colors:
  • NATURAL

  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…

(2)
$72.00

  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…

(5)
$80.00

  Classic styling and skilled craftsmanship make the Bailey 1922 Salem Braided Fedora a style to be proud to own. As featured on GQ.com, the soft/packable sewn braid construction, pinched front crown, with striped grosgrain band of the Salem qualify this fedora as a carryover classic. This…

$75.00

  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 Billy Braided Toyo Straw Fedora Hat is a top selling topper…

$66.00

  Stay stylish with the Noakes Toyo Straw Fedora Hat from Bailey. This light-weight hat features a simple, almost minimalist design, made of durable, comfortable toyo straw, complimented by a single Bailey side label. It's all tied together by a solid stripe of color wrapping around the…

$80.00
Available Colors:
  • NATURAL
  • BROWN

…  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…

$62.50
Available Colors:
  • HONEY
  • SILVER

  Made in the 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…

$76.00
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

  Handwoven in Ecuador; Finished in the USA   Caramel-hued and expertly crafted, the Tessier Panama Straw Fedora Hat by Bailey will add distinctive style to your look this spring and summer! Like all genuine panama hats, the Tessier's body was artfully handwoven in Ecuador then…

(2)
$170.00

…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)
$170.00
Available Colors:
  • NATURAL

…luxurious Bailey custom woven polyester sweatband that conforms to your brow, inasmuch as your look conforms to anything but your own fashion standards.   Approx. 3 1/2" Teardrop Crown 1 5/8" Snap Brim   Made of: 100% Polypropylene Braid   Black Bailey Side Pin Striped…

(6)
$75.00

  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…

$175.00
Available Colors:
  • NATURAL

  Made in the USA The Bailey Hanson Shantung LiteStraw Fedora Hat is not your typical stiff straw hat. Crafted in the USA using their exclusive LiteStraw® finish, the Hanson has a soft and supple feel that rivals much-celebrated Panama straw hats with the added benefits of water…

$140.00
Available Colors:
  • NATURALBLACK

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

(2)
$75.00

…  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.   FINAL SALE  

(1)
$67.50
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

…Look no further than the striking Tasmin Panama Straw Fedora Hat by Bailey! All genuine panama hats, including the Tasmin, are handwoven by artisans in Ecuador; the Tasmin was then blocked and finished in the USA by expert Bailey craftsmen. The Tasmin's multi-color braided inlaid crown insert helps…

(2)
$175.00
Available Colors:
  • MULTI
  • BLUE

…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! …

$230.00
Available Colors:
  • NATURAL

…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…

$175.00
Available Colors:
  • NATURAL

…  Handwoven in Ecuador Blocked & Finished in the USA Vented Crown Detail - For Style & Breathability Japanese Grosgrain Ribbon Hat Band with Side Bow Small Bailey Logo on Side Bow Woven Sweatband Bailey Crown Tip Inner Label   Sizes: S, M, L, and XL; fits true to size.  

$180.00
Available Colors:
  • NATURAL

  The Denney Toyo Straw Blend Fedora Hat from Bailey is simple, with just a touch of flair! By flair, we're referring to the thin leather hat band wrapping around the crown, which nicely compliments the wide grosgrain ribbon hat band layered beneath it. The cotton twill sweatband is so…

$83.00
Available Colors:
  • BLACK
  • LATTE

  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 Billy Braided Toyo Straw Fedora Hat is a top selling topper…

(26)
$75.00

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey 1922 Blixen Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish gives the hat…

(3)
$118.00
Available Colors:
  • BLACK
  • NAVYBLUE
  • COGNAC
  • BASALT
  • SILVERBELLY

…Made in the USA   Featuring Bailey's proprietary Elite Finish, the Winters Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably supple…

(3)
$175.00

  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

…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.  

(1)
$175.00

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