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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 (195)

Bailey

1 - 28 of 195 Products
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  There's not much sharper than the Berle Toyo Straw Blend Fedora Hat from Bailey! This neat hat's most eye-catching feature is its clean, striped grosgrain ribbon hat band wrapping around the vented toyo crochet crown. Plus, the cotton twill sweatband and unlined interior allow for a nice…

$85.00
Available Colors:
  • NAVYBLUE
  • VANILLA

…100% Shantung LiteStraw®    Made in the USA Exclusive LiteStraw® Finish - Lightweight & Water Repellent Navy & gray Striped Hat Band w/ Side Bow Bailey Side Pin DRI-LEX® Absorbent Sweatband Bailey Crown Tip Inner Label   Sizes: S, M, L, and XL; fits true to size.  

(1)
$135.00
Available Colors:
  • NATURALBLUE

  Featuring a masculine distressed finish, the Lazar Suede Leather Ivy Cap is a deluxe flat cap by Bailey of Hollywood. Crafted of genuine pig skin leather with a distressed suede finish, the Lazar is a distinctive cap for flat cap lovers. Four small panels comprise the back half of the cap…

(1)
$90.00
Available Colors:
  • COFFEE

  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.…

$100.00
Available Colors:
  • NATURAL

  Classic 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.…

$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…

(3)
$158.00

…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 snapped…

$52.50
Available Colors:
  • CHARCOAL

  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

  Bailey's cap shapes & fits are unparalleled when it comes to quality and style. The Harston Linen Ivy Cap, in woven linen makes for a unique shape that creates a smart look which can be dressed up for evening or dressed down for a casual look. There will be no other cap that fits this…

(6)
$55.00
Available Colors:
  • BEIGE
  • CHAMBRAY

…the USA   A classic pinch crown fedora hat with a few luxurious touches, the Flume Velour Fur Felt Fedora Hat by Bailey is a sumptuous new offering from Bailey of Hollywood. Trimmed with a smooth leather hat band and removable black side feather, the Flume is simply breathtaking. A…

$350.00
Available Colors:
  • AUBERGINE
  • BLACK
  • MINK

  Made in the USA   The new Bankhead Wool Felt Fedora Hat by Bailey features their exclusive 606 Finish for a luxurious sheen and feel. Crafted of the finest 16-micron wool, felts destined for the premier 606 finish are blended, double carded, and hand wet felted. Afterwards, a light…

$81.00

  Made in the USA   Bailey Hat's most popular fedora. This premium wool felt is created with their exclusive blend of 100% virgin wool fibers, specially finished by their skilled craftsmen resulting in superior quality and unequaled value.   Approx. 4" crown 2 1/2" snap…

(4)
$120.00
Available Colors:
  • BLACK

  Bailey introduces the Craig Straw Fedora Hat, a new straw fedora for the spring and summer season. Crafted of packable polypropelene straw, the Craig Fedora is lightweight, packable (flexible) and water resistant. The Craig Fedora Hat is ideal for both men and women and is a great option for…

$72.00
Available Colors:
  • GRAPHITE
  • NATURAL
  • RED

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

$98.00

…Cap by Bailey!   Approx. 10 1/4" Length, Flat 8 1/4" Width, Flat 2 1/4" Extended Sewn Bill/Brim    Made of: 100% Cotton    Classic 8-Panel Newsboy Design Extended Sewn Bill/Brim Small Wooden Bailey Side Pin Comfort Sweatband Linen/Cotton Blend Lining w/ Bailey Crown…

$60.00
Available Colors:
  • BLUEWHITE

…outdoorsman crown -  a mix between traditional pinch and teardrop crowns - the Lapkus Wool Felt Fedora Hat by Bailey is an eye catcher. Finished with a Japanese grosgrain ribbon hatband, small Bailey side pin and cotton sweatband - the Lapkus is also both packable and water repellent.    …

$90.00
Available Colors:
  • COGNAC

  New to the Bailey Galvin design, the Galvin Striped Twill Wool Newsboy Cap features a stylish striped tweed pattern perfect for the season. Featuring the Galvin's classic newsboy design, this cap boasts an 8-panel crown, Bailey back pin and a double snap bill. Great for cool fall and winter…

$100.00
Available Colors:
  • CHARCOAL

  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

  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

…Blend Pork Pie Hat by Bailey features a crocheted toyo straw and polyester blend. The result is a pleasing fabric/straw hybrid that allows air to circulate and helps keep you cool during warm spring and summer seasons. Accented with a simple layered fabric hat band and small Bailey staple side pin,…

$80.00
Available Colors:
  • CHARCOAL
  • NATURAL

…Remick Toyo Straw Pork Pie Hat by the one and only Bailey!    Approx. 3 3/4" Telescope Optimo Crown 2" Snap Brim   Made of: 100% Toyo Straw   Made in the USA Two-Tone Weave Grosgrain Ribbon Hat Band w/ Side Bow Bailey Micro Staple Side Pin Printed Fabric Sweatband…

$90.00
Available Colors:
  • NAVYBLUE

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

$98.00

…bring with you anywhere with Bailey's Sobel Newsboy!   Approx. 9 3/4" Length, Flat 10" Width, Flat 2" Soft, Sewn Bill   Made of: 100% Cotton   Soft & Flexible 8-Panel Design No Center Top Button Textured Crown / Jersey Bill Bailey Micro Staple Side Pin Cotton Twill…

(1)
$60.00

  Art is alive with the Anthem Velvet Ivy Cap from Bailey of Hollywood. The clean design is finished with a beautiful corduroy and velvet texturing. Be your stylish self with the lined interior showcasing beautiful line art!   Approx. 9" Diameter 2" Pre-Curved Sewn Bill/Brim …

$60.00
Available Colors:
  • CHOCOLATEBROWN

  This isn't your average ball cap, this is the Busby Suede Baseball Cap from Bailey of Hollywood! Made of 100% leather, this cap has breathable eyelets and a comfort sweatband, and the adjustable strap in back makes this cap perfect for everyone!   Approx. 4 3/4" Crown 2 3/4"…

$95.00
Available Colors:
  • CHOCOLATEBROWN

  There's just something comforting about the Bernick Wool Blend Baseball Cap from Bailey of Hollywood. Maybe it's the classic buckram supported front panels, maybe it's the comfortable and cushioned sweatband, or maybe it's the adjustable snap strap in the back. Whatever it is, this hat is…

$60.00
Available Colors:
  • OLIVEGREEN
  • BURGUNDY

  Made in the USA   Bailey's Browtine Wool LiteFelt Safari Fedora Hat is part of their rugged Wind River® Collection of hats. The Browtine is crafted in the USA using Bailey's exclusive wool LiteFelt® finishing process to create a hat that is lightweight, packable, crushable and water…

$72.00
Available Colors:
  • SERPENT

  Made in the USA   The Harvey Shantung Straw Fedora Hat by Bailey offers a quirky and singular style not often seen in fedoras. The Harvey Fedora is crafted of firm shantung straw and boasts an intricate vent woven crown (sides). Its wide brim is offset with a twisted, reversible…

$140.00
Available Colors:
  • NATURAL

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