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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 (203)

Bailey

1 - 28 of 203 Products
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…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…

(1)
$145.00

…The Doty Wool Felt Cattleman Western Hat by Bailey features their exclusive new 606 Finish that takes the world's finest 16-micron wool and blends, double cards and extra hand wet felts it to give it an incredibly soft and lustrous finish. Part of Bailey's rugged Poet® Collection, the Doty Western…

$120.00

…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…

$59.50
Available Colors:
  • CHARCOAL

  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.…

$55.00

  You can get comfortable with the Beech Wool Blend Newsboy Cap from Bailey of Hollywood. The classic 8-panel newsboy design features a herringbone stitching, as well as a flat bill/brim complete with a snap button. Nothing says "old-timey style" quite like this cap!   Approx. 10"…

$64.00

  Introducing the Bailey Archer Toyo Straw Braid Fedora Hat with a stingy (short) snap brim for a sleek look. Crafted of a lightweight and flexible toyo straw blend, the Archer is a great alternative to classic straw fedoras that are prone to cracking and crushing.    Approx. 3 3/8"…

$57.38
Available Colors:
  • SMOKE
  • COFFEE

…3" Brim - Front & Back 2 3/8" Brim - Sides   Made of: 100% Wool Felt   Leather Hat Band & Loop with Bronze Buckle Oval Bailey Pin Cotton Sweatband Inner Bailey Leather Crest Patch Unlined Water Repellent Packable (Shape Retentive)   Sizes: S, M, L and XL  

(2)
$100.00

…flat cap from Bailey of Hollywood. The Lord features a pair of metal snaps to keep the front of the crown snug against the bill for the quintessential sleek cap profile. If you want an unconventional but still striking appearance, just open up the snaps. The simplicity of the Bailey of Hollywood…

$83.00
Available Colors:
  • BLACK
  • CHARCOAL
  • BROWN
  • CAMEL

  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…

(3)
$46.75
Available Colors:
  • BEIGE
  • CHAMBRAY

…The Bailey Seddon Wool Blend Ivy Cap is the perfect hat for someone that loves the cuts of the newsboy cap with 8/4 panels but doesn't like the button on top.   Approx. 9 1/2" Diameter 2" Sewn Bill/Visor   Made of: 50% Wool 50% Polyester   6-Panel Design Bailey Staple…

(1)
$53.55

…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)
$59.50

…Introducing the Bailey Mannesroe fedora that adds a little color and style to your life. It is a great hat to spend the day walking around town in without feeling over heated. Approx. 4" Center pinch crown Approx. 2" Snap brim Made of: 100% Polypropylene Unlined Bailey pendant …

(1)
$51.00

…Hat by Bailey is a handsome new style for fall and winter. The Goldring is crafted in the USA of premium wool LiteFelt® for a soft, packable/crushable and water repellent finish. Its classic pinch crown is adorned with a striped grosgrain ribbon hat band with a fold-over side detail and Bailey micro…

$76.50
Available Colors:
  • NAVYBLUE
  • SILVERBELLY

…soft and luxurious Bailey custom woven polyester sweatband that conforms to your brow, inasmuch as your look conforms to anything but your own fashion standards.   Approx. 3 1/2" Crown 1 5/8" Brim   Made of: 100% Polypropylene Braid   Black Bailey Side Pin Striped…

(3)
$60.00

  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.…

$76.50

  Made of crisp cotton in a medley of fun, bright colors, Bailey's Keter Cotton Ivy Cap is a new style for spring and summer. Crafted with a unique 6-panel design, the Keter Ivy Cap is trimmed with a small Bailey staple side pin, single snap bill and custom printed cotton lining. Add color and…

(3)
$52.00

  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)
$55.00

  The Sanville Cadet Cap from Bailey of Hollywood is the epitome of an instant classic. The iconic cadet cap design is complimented by breathable eyelets in the back, a comfort sweatband, and patterned interior lining. Simplicity is key!   Approx. 4" Crown 2 1/4" Precurved…

$54.00

…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…

$114.75

The Jett Porkpie combines a classic men's style, with Bailey's fashion forward Jett Nap Finish. These premium wool felts are crafted with Bailey's exclusive blend of 100% virgin wool fibers and a unique silk-like finish, adding a luxurious sense and character. The hat comes fully lined in satin. 4"…

$110.00
Available Colors:
  • BLACK

…wooden Bailey side pin, cotton sweatband and lining, and a sewn Bailey crown tip label.    Approx. 9 3/4" Length, Flat 10" Width, Flat 2" Sewn Bill   Made of: 100% Cotton   6-Panel Duckbill Design Wooden Bailey Side Pin Cotton Sweatband & Lining Sewn Bailey Crown…

$42.50
Available Colors:
  • RED

  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…

(3)
$55.25

  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

…color in this style is quite dark and is only a shade lighter than the Black color when placed side by side.    Made in Italy Bailey of Hollywood, provider of hats to the Hollywood elite since 1922, grabs a hat style and infuses every incarnation with quality and class. The…

$85.00

  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…

$55.25
Available Colors:
  • GRAPHITE
  • NATURAL
  • NAVYBLUE
  • RED

  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…

$97.75
Available Colors:
  • NATURALBLACK

  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…

$51.00
Available Colors:
  • OLIVEGREEN

…by Bailey!    Approx. 3 7/8" - 4" Tear Drop Crown 2 3/8" - 2 1/2" Snap Brim   Made of: 100% Shantung LiteStraw®   Made in the USA Premium LiteStraw® Finish - Supple Feel & Water Repellent Center Fold Overlay Hat Band w/ Side Bow Small Side Feather (Removable) Bailey

$102.00
Available Colors:
  • NATURAL

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