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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 (98)

Bailey Trilby

1 - 28 of 98 Products
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  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…

$59.50

  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…

(22)
$55.00

  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)
$65.00

  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…

(1)
$59.50

  Introducing the Bailey Archer Toyo Straw Braid Fedora Hat with a stingy (short) snap brim for a sleek look. Crafted of a lightweight and flexible toyo straw blend, the Archer is a great alternative to classic straw fedoras that are prone to cracking and crushing.    Approx. 3 3/8"…

$57.38
Available Colors:
  • SMOKE
  • COFFEE

…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

  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…

(8)
$95.00

  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

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

(2)
$76.50

  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…

$95.00
Available Colors:
  • BLACK
  • PEWTER

…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

  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.…

$76.50

  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…

$52.50
Available Colors:
  • FORESTGREEN

  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%)…

$243.75
Available Colors:
  • CAMEL

…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)
$80.75

  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. …

$127.50
Available Colors:
  • NATURAL

  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…

$89.25

…  Bailey's unique Larsen Leather & Sisal Straw Fedora Hat boasts a singular design that combines lightweight sisal straw with smooth overlaid genuine leather. Crafted by expert Bailey craftsmen in the USA, the Larsen is simply breathtaking. A tonal side feather and Bailey staple pin…

$191.25
Available Colors:
  • NATURALBLACK

  You're comfortable and cool-looking when you're wearing the Stanley Fedora Hat from Bailey. This well-made fedora features a stiffened, dyed braid, a matching woven hat band with a Bailey metal side pin, and a comfortable cotton twill sweatband. If you want to turn heads, this hat is one…

$80.00
Available Colors:
  • DARKNATURAL

…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…

$160.00
Available Colors:
  • NATURAL

…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! …

$182.75
Available Colors:
  • NATURAL

…classic-width snap brim, traditional grosgrain ribbon trim and a Bailey staple side pin.   Ditch the plain straw fedoras this season and add a touch of personal style to your look with the Hartley Toyo Straw Fedora Hat by Bailey!    Approx. 3 7/8" Crown - Front 4 1/8" Crown -…

$82.50
Available Colors:
  • NATURALBLACK

…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" Crown 2 7/8" Pre-snap Brim   Made of: 100% Genuine Panama…

(4)
$123.25
Available Colors:
  • NATURAL

  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

  Made in the USA   Introducing the Kilgore Endura Toyo Straw Fedora Hat, part of the Bailey Wind River® collection of outdoor styles. The Kilgore is crafted in the USA using Bailey's exclusive Raindura finish that makes the straw both water resistant and shape retentive. The Kilgore…

$74.80
Available Colors:
  • TAN

…by Bailey!    Approx. 3 7/8" - 4" Tear Drop Crown 2 3/8" - 2 1/2" Snap Brim   Made of: 100% Shantung LiteStraw®   Made in the USA Premium LiteStraw® Finish - Supple Feel & Water Repellent Center Fold Overlay Hat Band w/ Side Bow Small Side Feather (Removable) Bailey

$102.00
Available Colors:
  • NATURAL

…two-toned geometric weave, the new Arsun Two-Tone Straw Fedora Hat by Bailey steals the show. The Arsun boasts a classic pinch front crown and mid-width brim combined with a simple grosgrain ribbon hat band and Bailey micro-staple side pin. Stylized venting woven along the crown's circumference…

$123.25
Available Colors:
  • BLACKWHITE

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