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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 (192)

Bailey Hats

1 - 28 of 192 Products
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Related Categories: Bailey | Bailey Of Hollywood

…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…

$121.55
Available Colors:
  • CHARCOAL

  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…

$103.00

  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…

$145.00
Available Colors:
  • KHAKI

  Made in the USA The Bailey Briar Fedora is a great basic to have in your collection of hats. Featuring a safari-inspired design, the Briar adds a few stylish updates including a tear drop crown and handsome leather hat band. Great for both men and women, the Briar adds…

(2)
$110.00

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

$102.00

…The Renegade® Lexington Wool Felt Western Hat by Bailey features a polished stiff wool felt finish for a crisp and handsome look that won't lose its shape. Crafted with a pinched tear drop crown, the Lexington is finished with a leather tassel hat band and a stylish, pre-shaped brim. The interior…

(2)
$94.00

Hat by Bailey features their exclusive new Raindura Finish which helps the hat maintain its shape even after getting wet. Pliable and completely packable, Rockett has a crease down its classic telescope crown and is finished with a braided hat band complete with side star pin and wooden Bailey side…

(2)
$110.00
Available Colors:
  • TAN

…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, and XXL; fits true to size.  

(5)
$120.00
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)
$165.00
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"…

$75.00
Available Colors:
  • BLACK
  • RUST

  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…

$35.40
Available Colors:
  • OLIVEGREEN

…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! …

$175.00
Available Colors:
  • NATURAL

  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…

$35.40
Available Colors:
  • BLACK

…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…

$170.00
Available Colors:
  • NATURAL

…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…

$75.00
Available Colors:
  • NATURAL

…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…

$63.75
Available Colors:
  • GRAPHITE

…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…

(4)
$125.00
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.   …

$170.00
Available Colors:
  • BLEACH

…together in the Gunnar Panama Straw Fedora Hat by Bailey. The innovative 2-toned hat band has been given a western rope feel thanks to the heavy thread topstitching. Blocked and finished in the USA of 100% of Panama straw, this hat is trimmed with a Bailey side pin and DRI-LEX® sweatband for added…

$190.00
Available Colors:
  • TAN

  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…

$110.00
Available Colors:
  • MOLE

…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

  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

  Combining toyo straw (paper) 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…

$65.00
Available Colors:
  • NATURAL

  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…

$78.00
Available Colors:
  • NATURAL
  • BROWN

…Western Hat by Bailey. This is another great example of the perfect look. The hat band blends with the hat which causes the minature belt buckle to truly shine.   Approx. 4 1/4" Cheyenne Crown  4" Raw Edge Brim   Made of: 100% Firm Wool Felt   Wool Felt Hat Band Lined…

$100.00
Available Colors:
  • BLACK

…This hat fits a little loose for each size Made in the USA Introducing the Navarro Wool Felt Western Hat by Bailey. This is a great hat for the true journey man. This piece will keep its shape throughout your trip and will keep you protected along the way. The hat band is…

(2)
$96.00

…Straw Outback Hat, part of the Bailey Wind River® collection of rugged outdoor styles. The Oswego is crafted in the USA using Bailey's exclusive Raindura finish that makes the straw both water resistant and shape retentive. The Oswego is lightweight and features a stylish woven fabric hat band and…

$90.00
Available Colors:
  • NATURAL

…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 with a stingy…

$56.10
Available Colors:
  • BLUE

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