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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 (92)

Bailey Fedora

1 - 28 of 92 Products
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  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…

(9)
$95.00

  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)
$98.00

…  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!   Approx.…

$215.00
Available Colors:
  • NATURAL

  Made in the USA   Introducing the versatile and stylish new Briles Wool Felt Open Crown Fedora Hat by Bailey! Crafted of soft and packable wool felt, the Briles features an open crown design that can be shaped into different styles with ease. Its moldable crown is untrimmed to allow…

$135.00
Available Colors:
  • BLACK

  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…

$59.50
Available Colors:
  • COPPER
  • BLACK
  • NAVYBLUE
  • SAND

…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
  • PEWTER

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

(4)
$66.00

…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…

(2)
$145.00

  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)
$72.00

…  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…

(1)
$89.25
Available Colors:
  • BLACK

…in good taste, the Bailey of Hollywood Dalton outback fedora gets you out there.    Approx. 4 1/4" Crown 2 5/8" Brim   Made of:  65% Polyester 35% Cotton   Unlined Padded cotton sweatnand Side eyelets Leather headband with prong back Bailey oval pin Water repellent …

(19)
$51.00
Available Colors:
  • BLACK
  • NAVYBLUE

…  Inspired by nature, the Bailey of Hollywood Spencer Toyo LiteStraw Fedora Hat keeps the rain out and style always on. This toyo design features their exclusive LiteStraw® finish for an amazingly comfortable feel in addition to water repellency. With Bailey's LiteStraw® finish your perception…

(2)
$85.00

  Kick back and relax with the Hester Toyo Straw Blend Fedora Hat from Bailey! This fedora features a cotton twill sweatband, as well as an unlined interior, making it one incredibly comfortable hat. Most notably, the grosgrain ribbon hat band has a stunning striped detail.   Approx.…

(1)
$80.00
Available Colors:
  • COPPER

Made in the USA The Bailey Guthrie is made of a new softening and finishing technology for Shantung Straw which creates an incredibly comfortable and flexible fit. As an added bonus, this is one of the few straw hats that is actually water resistant. The hat comes with the Dri-Lex moisture…

(3)
$130.00
Available Colors:
  • NATURALBLACK

  Made in the USA   Charm and style are one, when it comes to the Bailey Brandt Lanolux Wool Felt Fedora Hat. You'll be walking tall with confidence in this center dent fedora with leather trim hat band!   Approx. 3 3/4" Crown 2 1/2" Brim   Made of: 100% Wool Felt -…

$130.00
Available Colors:
  • BLACK
  • TAUPE
  • WALNUTBROWN
  • BLUE
  • BLACKMIX

…  Multi-colored with a unique patterned weave, the new Giger Panama Straw Fedora Hat will take your breath away. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert Bailey craftsmen, the Giger's striking good looks are no accident. Its natural, caramel,…

(1)
$190.00

  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"…

$65.00
Available Colors:
  • BLACK
  • RUST
  • BLUE

  Made in the USA   Introducing the new Packable LiteFelt Wool Fedora Hat by Bailey! Part of their Bailey by Hollywood classic men's line, the new Packable Fedora is exclusively sold at the Village Hat Shop and features their premium LiteFelt® for a soft, packable and water repellent…

(1)
$98.00
Available Colors:
  • BLACK
  • RED
  • GRAPHITE

…wool felt Ammon Wool Felt Teardrop Fedora Hat by Bailey is astonishingly silky to the touch. A classic teardrop crown (aka C-Crown) and all around down-sloping brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband and…

$135.00

  Made in the USA   Crafted with an extra wide brim and Bailey's Elite stiffened finish, the new Colver Elite Wool Felt Fedora Hat is a handsome new style for fall and winter. Starting with a classic tear drop crown, the Colver is trimmed with a narrow Japanese grosgrain hat band,…

$140.00

  Made in the USA   Bailey's new Hereford Elite Wool Felt Fedora Hat is crafted using the finest wool available from Bailey. Soft, lightweight, packable and crushable – the Hereford has it all. Its elongated tear drop crown gives a distinctive edge to the style and is finished with a…

$140.00

…  The new Lanth Polished Wool Felt Fedora Hat by Bailey boasts luxurious polished wool for incredible softness and a lovely sheen while remaining completely packable. Its classic tear drop crown design is trimmed with a wool felt hat band, micro Bailey staple side pin, comfort sweatband and…

$114.75
Available Colors:
  • OXBLOOD
  • BLACK

…Made in the USA   Featuring Bailey's proprietary Elite Finish, the Bogan 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…

$135.00

  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…

$59.50

…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 Curtis Wool Felt Safari Fedora Hat is one of the most practical hats in the Bailey line. The classically designed safari fedora repels water and oil based spills. It is breathable, and durable and can be packed for ease of travel.    Approx. 4" Center…

(1)
$98.00

…Exclusive Color   Made in the USA   Introducing the new Packable Wool LiteFelt Fedora Hat by Bailey! Part of their Bailey by Hollywood classic men's line, the new Packable Fedora is exclusively sold at the Village Hat Shop and features their premium LiteFelt® for a soft, packable…

$83.30

…styling and skilled craftsmanship make the Bailey of Hollywood 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 fantastic,…

$66.00

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