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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 (108)

Bailey Trilby Hats

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…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 LiteFelt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines traditional craftsmanship…

(13)
$130.00
Available Colors:

  Street-wise and ready for action, the Bailey 1922 Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and style. The teardrop…

(8)
$85.00

…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 teardrop crown and all-around snap stingy brim. A striped inlaid "hat band" adorns the…

(6)
$90.00

…with the Caprole Wool LiteFelt Walker Trilby Hat by Bailey 1922! The Caprole is a unique trilby that is water resistant, stain repellent, and shape retentive making it ideal for styling anywhere you go. It includes a removable side duck feather, a Bailey metal pin, and a unique grosgrain ribbon…

$123.25

…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…

(2)
$80.00

  Made in the USA   Elevate your style with Bailey 1922’s best-selling Tino Wool Litefelt® Trilby Fedora Hat. Handcrafted in the USA and made with the iconic and durable LiteFelt®, a treatment process on wool that makes it not only water repellant, but also retains its shape. A…

$110.50

…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 LiteFelt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines traditional craftsmanship…

$94.40
Available Colors:
  • RUST

  Made in the USA   Bailey 1922 presents the Tino Wool LiteFelt Trilby Fedora Hat, a sophisticated and classy-looking hat! Hand-crafted in the U.S.A., this hat is practical for everyday wear as it is both water-repellant and packable, ideal for any weather worldwide, so you can take…

$110.50
Available Colors:
  • MOSS

  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…

$75.00
Available Colors:
  • NATURAL

…Straw Fedora Hat by Bailey! Panama hats are a summer wardrobe staple but what makes the Cuban so unique is the two-toned Japanese grosgrain ribbon pug hat band. It's refined, it's modern, it's comfortable! Celebrate the art of hat-making and sharp dressing with the Cuban by Bailey.   …

$220.00
Available Colors:
  • BLEACH

…your normal hat size.   Made in the USA   The Burnell LifeFelt Wool Fedora Hat by Bailey features a classic fedora silhouette with Bailey's top-rate LiteFelt® finish making the wool water repellent, shape retentive and durable. The wide Japanese grosgrain ribbon hat band has been…

$94.50
Available Colors:
  • NATURAL

…Crown your restless spirit with the new Ashmore Wool LiteFelt Fedora Hat by Bailey! Part of their Poet® Travel Collection inspired by the spirit and grit of the Old American West, Ashmore is crafted in the USA using Bailey's exclusive wool LiteFelt® that is soft, packable/rollable, water repellent…

(1)
$60.00
Available Colors:
  • BLACK

…in Ecuador   Bailey's Bystrom Panama Straw Fedora Hat, made out of 100% toquilla palm leaves, has come to stand out. A leather cord hat band and a pop of contrasting color on the pinch front crown provides a unique and versatile style. A uniquely made Panama hat with a timeless look! …

$191.25
Available Colors:
  • TAWNY

  Made in the USA   May we present Bailey's Sterne Wool Felt Fedora Hat! This 3" stiff flat brim features a Japanese grosgrain ribbon hat band, braided cord overlay which has been secured in a fashionable knot. The raw edge brim is sharp and modern while the leather sweatband and…

$127.50
Available Colors:
  • KHAKI

…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…

(1)
$220.00
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…

$170.00
Available Colors:
  • NATURALBLACK

…the USA   The Nilson Fur Felt Fedora Hat is from Bailey is part of their Superior Fur Felt collection. Features a Japanese grosgrain ribbon hat band with an origami half bow. This is finished with a vintage flooring nail. This is a Bailey favorite, full of elegance and comfort.   …

$361.25
Available Colors:
  • SLATE
  • ARMYGREEN
  • COPPER

…grosgrain band overlaid with a vintage leather cord. Further detailing includes a Bailey micro side pin and moisture-wicking sweatband. Can elegance be functional? Yes, with the Lachlan Raindura Straw Fedora Hat by Bailey!   Approx. 4 1/2" Tear Drop Crown 2 7/8" Flat Underwelt Brim …

$170.00
Available Colors:
  • TAN

…with tonal ribbon overlay, narrow crosspiece detail ideal for holding a golf pencil, and a Bailey micro side pin. Get out on the green in style this season with the Daxton Seagrass Straw Fedora Hat by Bailey!   Approx. 4" Tear Drop Crown 3 1/2" Upturned, Overwelt Brim   Made of:…

$170.00
Available Colors:
  • SEAGRASS

…may be some variance from hat to hat and is part of its beauty and uniqueness.   Made in the USA   The Glaser Sisal LiteStraw Fedora Hat by Bailey is a great choice for sun protection. With a 3" flat brim and Bailey's famous LiteStraw® finish, this hat not only protects you from…

$195.00
Available Colors:
  • NATURAL

…beautiful cool toned colors, the Magness LiteStraw Fedora Hat by Bailey is made of 100% shantung straw which has been finished with innovative LiteStraw technology. The Magness is a stiff fedora and has been crafted using colorblocking. The hat band is made of Japanese grosgrain ribbon and a dipped…

$153.00
Available Colors:
  • SILVER

…band and with Bailey embossed logo.     Approx. 4" Center Pinch Crown 2 7/8" Pre-Snap Brim   Made of: 100% Panama Straw (Toquilla Palm) Cuenca Weave     Handwoven in Ecuador Panama Straw - Cuenca Weave Blocked and Finished in the USA Leather Hat Band Woven…

(4)
$190.00
Available Colors:
  • NATURAL

…Straw Fedora Hat by Bailey, a fedora that will keep you cool and protected this summer. Made in the USA of 100% shantung straw, lightweight yet strong, the Relik is finished with LiteStraw® that provides a supple feel, water repellent, and shape retention. A Japanese grosgrain ribbon hat band with…

$175.00

…Finished in the USA   The Horan Panama Straw Fedora Hat by Bailey is a finely woven, lightweight headwear creation. This is hot weather perfection and will keep you cool, calm and collected. With a beautiful embossed leather hat band and delicate ventilation detailing on the crown, the…

$240.00
Available Colors:
  • NATURAL

  Made in the USA Bailey's Winstone Raindura Straw Fedora Hat is the most shape retentive, durable straw hat on the market thanks to the exclusive Raindura® finish. This revolutionary process involves thermosetting yarn which has been handwoven inside a straw body. It is then blocked…

$135.00
Available Colors:
  • NATURAL

…USA   With the Racer Panama Straw Fedora Hat by Bailey you get both comfort and style. This is a custom panama handcrafted in Ecuador with a woven crochet teardrop crown and brisa snap brim. Finishing touches are the Japanese grosgrain ribbon hat band and finely woven sweatband. The Racer…

$225.00
Available Colors:
  • NATURAL

…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 blocked and finished in the USA by master craftsmen. The resulting hat is lightweight, supple and…

(2)
$220.00

…Part of Bailey's timeless 1922 collection, the Brooks Panama Straw Fedora Hat exemplifies enduring taste. The hat body is handwoven in Ecuador of genuine panama straw in a classic Cuenca weave pattern then blocked and finished in the USA. Simply trimmed with a two-tone grosgrain ribbon hat band, the…

$119.00

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