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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 (155)

Bailey Hats

1 - 28 of 155 Products
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  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…

$70.00
Available Colors:
  • NATURAL
  • BROWN

…the Derian Raindura Straw Outback Hat by Bailey features their exclusive new Raindura finish which helps the hat maintain its shape even after getting wet. Lightweight, pliable and completely packable, Derian is finished with a pattern woven hat band and Bailey side pin. Inside, an absorbent…

(1)
$110.00

…A handsome multi-colored striped hat band gives Bailey's Tharp Shantung LiteStraw Fedora Hat a singularly striking spring/summer feel. Proudly crafted in the USA using their exclusive LiteStraw® finish, the Tharp is a soft, lightweight and water repellent straw hat blocked into a stylish tear drop…

$114.75
Available Colors:
  • NATURALBLUE

…braided waxed cord hat band, Sturges is finished with a Bailey-branded leather closure, an underwelt brim and adjustable sweatband. Take on the outdoors with confidence while wearing your handsome and functional Sturges LiteFelt Fedora, part of Bailey's rugged Poet® collection of hats.    …

(1)
$89.25

…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)
$89.25
Available Colors:
  • BLACK

  Village Hat Shop 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…

$83.30

  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)
$66.00

…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 traditional craftsmanship…

(9)
$95.00

…and unequaled value.   Approx. 4" crown 2 1/2" snap brim   Made of: 100% Wool Felt - Stiff Finish   Grosgrain ribbon hat band Removable side feather Bailey imprinted on hat band Satin Lining Poly Blend Sweatband   Sizes: S, M, L, XL, XXL and XXXL  

(4)
$110.00
Available Colors:
  • BLACK

…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% Genuine Panama Straw (Cuenca Weave)   Leather Hat Band Woven Polyester…

(4)
$155.00
Available Colors:
  • NATURAL

  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

…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 great look!   Approx. 4"…

$80.00
Available Colors:
  • DARKNATURAL

  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

  A classic bucket hat from Bailey, the Clapcott Rain Bucket Hat has a few added features for extra functionality. Its water resistant fabric helps keep you dry while the back of the crown boasts a storage zipper to handily store your cash, ID or credit cards. Inside, the Clapcott is fully…

$45.00
Available Colors:
  • BLACK

…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 quality! …

$170.00
Available Colors:
  • NATURAL

…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…

$160.00
Available Colors:
  • NATURAL

…ready for something new with the Melton LiteStraw® Seagrass Gambler Hat from Bailey! This unique hat is made with seagrass, a durable and stain-resilient material perfect for any stylish adventurer. No matter your plans, this hat should be your go-to!   Approx. 3 1/2" Telescope Crown 3…

(2)
$120.00
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

…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 custom…

$114.75
Available Colors:
  • OXBLOOD
  • BLACK

…option for those looking for a hat with the look of straw, without the hassle straw hats require. What's not to love?    Approx. 3 7/8" Pinch Crown 2" - 2 1/8" Snap Brim   Made of: 100% Polypropelene   Grosgrain Hat Band Bailey Staple Side Pin Cotton Twill Sweatband…

$72.00
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE
  • RED

  Made in the USA Introducing the Jericho 3x Western Hat by Bailey. This piece is truly gorgeous. The hat band was created with pieces of leather attached to one another by three metal accent links on the front. The inside is lined to make sure it will keep you warm during those…

$100.00
Available Colors:
  • MOLE

…intricate, 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…

$123.25
Available Colors:
  • BLACKWHITE

…ultra light water repellent coating. The result is the most shape retentive, durable straw hat in the market.  Showcasing a thin leather hat band with stitching, as well as a Bailey side pin, this hat is high quality. Plus, the padded sweatband and unlined interior are very breathable and…

$120.00

  The Bailey Telemannes Pork Pie Hat is a modern interpretation of the timeless pork pie hat. Constructed from their proprietary mixed-color braiding and offset with an inset contrasting solid band, the Bailey Telemannes Pork Pie Hat separates itself from the pack with its bold and multicolored…

(4)
$32.50

…light water repellent coating. The result is the most shape retentive, durable straw hat in the market. This durable hat features a faux leather braided hat band, as well as a Bailey side pin. Made in America, this hat is absolutely high quality!   Approx. 3 1/2" Teardrop Crown - Front 3…

$120.00
Available Colors:
  • IVORY
  • NATURAL

…  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. 4"…

$215.00
Available Colors:
  • NATURAL

…loose. Made in the USA Introducing the Dynamite Wool Felt Western Hat by Bailey. This cowboy hat is equpped with a dri-lex sweatband to make sure that if you are getting a little hot your hat isn't going to show proof of that happening.   Approx. 4 1/2" Cheyenne…

$88.00
Available Colors:
  • BLACK

  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

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