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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 (105)

Bailey Trilby

31 - 60 of 105 Products
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  Handwoven in Ecuador, Finished in the USA   Quality matters, like with the Parson Panama Straw Fedora Hat from Bailey. This fine hat features a thin cotton herringbone hat band, as well as a contrast color bound edge around the brim. This USA-made fedora is of the highest…

$170.00
Available Colors:
  • NATURAL

  Made in the USA The Bailey of Hollywood Hiram Wool Felt Fedora Hat is made with a doeskin wool felt which is a premium felt that is lightly stiffened to add a crispness to the shape and finish. You don't want to crush this piece but it is not too stiff that it will feel…

$106.25
Available Colors:
  • BLACK

  The Denney Toyo Straw Blend Fedora Hat from Bailey is simple, with just a touch of flair! By flair, we're referring to the thin leather hat band wrapping around the crown, which nicely compliments the wide grosgrain ribbon hat band layered beneath it. The cotton twill sweatband is so…

$75.00
Available Colors:
  • BLACK

Bailey's new Maddow Shantung LiteStraw Fedora Hat is part of their rugged yet sophisticated Breed® Collection of hats and caps. The Maddow's uniquely worn finish is achieved by dyeing then hand-bleaching each hat for a singular gradient finish that adds style and personality. Crafted of Bailey's

$85.00
Available Colors:
  • BLACK

…vibe, the new Rayney Two-Tone Panama Straw Fedora Hat by Bailey boasts a singular new look for spring and summer. Crafted of genuine panama straw handwoven by artisans in Ecuador then expertly blocked and finished in the USA by Bailey craftsmen, this style is a handsome example of wearable art.…

$114.75
Available Colors:
  • NATURALBROWN

…Look no further than the striking Tasmin Panama Straw Fedora Hat by Bailey! All genuine panama hats, including the Tasmin, are handwoven by artisans in Ecuador; the Tasmin was then blocked and finished in the USA by expert Bailey craftsmen. The Tasmin's multi-color braided inlaid crown insert helps…

$136.00
Available Colors:
  • MULTI

  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

…Fedora Hat by Bailey is a new addition to their famed Poet® collection inspired by the grit and spirit of the Old American West. Rhode features an eye-catching custom hat band that layers cording trim and is finished with a smooth leather closure laser-engraved with the Bailey logo. Its soft…

$84.15
Available Colors:
  • BLACKMIX

  Made in the USA   Crafted in the USA of Bailey's superior fur felt blend, the new Ralat Superior Fur Felt Fedora Hat offers a classic pinch front crown and a stylish, wide brim. Trimmed with a Japanese grosgrain ribbon hat band and vintage flooring nail side detail, the Ralat boasts…

$276.25
Available Colors:
  • TAUPE

  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…

$106.25
Available Colors:
  • BLACK

…Grade 3   Handwoven in Ecuador Blocked & Finished in the USA Vented Crown Detail - For Style & Breathability Grosgrain Ribbon Hat Band w/ Side Bow Small Bailey Logo on Side Bow Drylex® Moisture Wicking Sweatband Bailey Crown Tip Inner Label   Sizes: S, M, L and XL  

$212.50
Available Colors:
  • NATURAL

…look of the hat.    Made in the USA The Bailey Dean Packable Wool Felt Fedora Hat is great for the traveler on the go. Easy to pack and easy to take anywhere.  The Bailey Dean is the trendier version of the famous Bailey Jackman.     Approx. 3 3/8" Pinch Front Crown 2"…

$80.33

  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…

$91.80

  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 and water repellent.…

$61.20
Available Colors:
  • SERPENT

  Handwoven in Ecuador; Finished in the USA   Caramel-hued and expertly crafted, the Tessier Panama Straw Fedora Hat by Bailey will add distinctive style to your look this spring and summer! Like all genuine panama hats, the Tessier's body was artfully handwoven in Ecuador then…

$136.00

…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 …

$51.00

  Made in the USA   Keep things classic with the Cayuga Endura Straw Fedora Hat from Wind River by Bailey. This stunning fedora features a woven build of a toyo straw blend, as well as comfortable padded sweatband and breathable, unlined interior. Additionally, the braided rope hat…

$75.00
Available Colors:
  • TAN

  Introducing the Tavion Abaca Straw Braid Fedora Hat by Bailey. This is a great lightweight hat that is comfortable and won't weigh you don't. THe hat band is created as one with the hat to create one solid piece.   Approx. 4" Crown 2 3/4" Brim   Made Of: 100% Abaca…

$85.00
Available Colors:
  • NATURAL

…the USA   Looking for something a little different? Add a punch of style to your look with the Gravely Straw Wide Brim Fedora Hat by Bailey! Featuring lightweight straw in gray and white interwoven for a unique and handsome finish, the Gravely is sure to make heads turn! Stylized venting…

$119.00

…USA Bailey of Hollywood is bringing to life the center dent sting brim fedora. Making the world of casual wear look a little more refined. Approx. 4" center dent crown Approx. 2" snap brim Made of: 100% toyo straw Unlined Dri-lex band Grosgrain ribbon Bailey side…

$59.50

  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

  Made in the USA Introducing the Fernley Shantung LiteStraw Fedora Hat by Bailey of Hollywood. Made of supple shantung straw, this style boasts Bailey's exclusive LiteStraw® technology for a soft and water repellent finish. Perfect for those who prefer wide-brimmed hats but hate…

$102.00

…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.    …

$76.50

  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

Bailey.    Approx. 3 3/4" Tear Drop Crown - Front 4" Tear Drop Crown - Back 2" Underwelt, Snap Brim    Made of: 100% Shantung LiteStraw®    Made in the USA Exclusive LiteStraw® Finish - Lightweight & Water Repellent Multi-colored Striped Hat Band w/ Side Bow Bailey

$102.00
Available Colors:
  • NATURALBLUE

…the USA   The Lydon Fur Felt Fedora Hat by Bailey is crafted from a beaver and rabbit fur blend felt with a rich and supple velour finish. A high 4-inch pinch crown is trimmed with a Japanese grosgrain ribbon hatband and small Bailey side pin. Its raw edge snap brim can be worn snapped up…

$255.00

…USA   The Cutler is a most excellent and stylish Cuenca weave Panama. This beauty from Bailey is the perfect casual summer fedora. It comes complete with a stunning leather band and Bailey hat pin.     Approx. 4" Crown 2 7/8" Pre-snap Brim   Made of: 100% Genuine Panama…

$123.25
Available Colors:
  • NATURAL

  Made in the USA The Bailey of Hollywood Noble Fur Felt Fedora Hat has a crown you don't see every day. This piece is a great hat to add to your collection because it is unique and is made to perfection.   Approx. 4" Crown 2 3/4" Brim   Made of: 100% Fur…

$297.50

…of the Bailey Hillman Wool Felt and Leather Fedora Hat features polished 100% wool felt with a lustrous satin finish in two great color combinations for a distinctively rugged and aged look. A tall, 4-inch teardrop or "Hondo" crown is set apart with a supple lambskin leather hatband and small Bailey

$122.40

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

$102.00
Available Colors:
  • NATURALBLUE

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