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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 (69)

Bailey Straw Hats

1 - 28 of 69 Products
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…unique look on today's modern man.   Approx. 4" Crown 2" Snap Brim   Made of: 55% Toyo Straw (Paper) 45% Polyester   Multi-Color Striped Grosgrain Ribbon Hat Band Bailey Side Pin Cotton Sweatband Unlined Packable / Crushable   Sizes: S, M, L, XL, and XXL; fits…

$66.00

…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. Its loose weave…

$100.00

…Made in the USA   The Cosmo Toyo LiteStraw Trilby Fedora Hat by Bailey features a finer weave than most other toyo straws in a classic and lightweight design perfect for spring and summer. Made in the USA with Bailey's famous LiteStraw® finish, the Cosmo is lightweight, flexible and water…

$125.00

…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 Straw (Paper)…

$80.00

…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…

$135.00

…  Approx. 4" Teardrop Crown 2 3/8" Brim Made of: 100% Genuine Panama Straw (Cuenca Weave)   Handwoven in Ecuador Blocked & Finished in the USA Double Layer Japanese Grosgrain Ribbon Hat Band Bailey Side Pin Fine Woven Sweatband   Sizes: S, M, L, XL, and XXL; fits…

$155.00

…& Finished in the USA   Featuring a lovely olive green hue, the Gelhorn Panama Straw Tear Drop Fedora Hat by Bailey is an artisanal gem. Handwoven by artisans in Ecuador of genuine panama straw, Gelhorn is then blocked and expertly detailed by talented craftsmen in the USA. Boasting a…

$150.00

hat band adds a touch of tradition.    Approx. 3 3/4" - 4" Tear Drop Crown 2 3/8" - 2 1/2" Snap Brim   Made of: 100% Genuine Panama Straw (Handwoven in Ecuador)   Finished in the USA Multi-Colored Patterned Weave Japanese Grosgrain Ribbon Hat Band with Side Bow Bailey

(1)
$190.00

…personality? 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…

(2)
$160.00

  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…

$130.00

  Street-wise and ready for action, the Bailey of Hollywood Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This short snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and…

(4)
$66.00

…than 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"…

$160.00

…Featuring Bailey's exclusive Winter Toyolene Braid, the new Ragon Toyo Braid Straw Trilby Fedora Hat features a sleek and modern design with an almost-clothlike feel and finish. Ragon features a trilby fedora design with an overall smaller profile, a color-blocked finish and no traditional hat band.…

$52.50

  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

…the USA   The Groff Vent Panama Straw Fedora Hat is a fresh new look from classic American hat purveyor, Bailey. Featuring a genuine panama straw hat body handwoven in Ecuador, the Groff is blocked into a classic pinch front crown fedora hat style and expertly finished in the USA. Trimmed…

$250.00

…including a grosgrain hat band with side bow adorned with a deluxe large side feather and antique flooring nail side detail. The Outen has all the acoutrements you love in a classic felt fedora with the lightweight and cooler wear of a straw hat. Made with Bailey's premium LiteStraw® finish,…

$115.00

…in a wool hat? Well now you don't have to. Introducing the Bailey Chaplin Panama Straw Bowler Hat with the heart of a bowler but the ability to keep you comfortable during the summer days.   Approx. 4" Bowler Crown 2" Curled Brim   Made of: 100% Genuine Panama Straw - Brisa Weave…

(2)
$150.00

  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

…fine toyolene braid, Bailey's Hooper Toyo Straw Blend Trilby Fedora Hat is not only incredibly breathable but also completely packable and crushable. Hooper features a color-blocked braided weave blocked into a tear drop crown and all-around snap stingy brim. A striped inlaid "hat band" adorns the…

(1)
$78.00

…colors but the plaid hat band make them sync perfectly together. You can't go wrong with this piece.    Approx. 4 1/2" Crown 2" Brim   Made of: 100% Ramie Straw   Lightweight Cotton Sweatband Unlined Plaid Cotton Hat Band Wood Chip Bailey Logo   Sizes:…

$48.75

…Toyo Straw Braid Trilby Fedora Hat by Bailey is great-looking, packable/crushable and lightweight. Its stylish color-blocked two-tone design gives this hat a unique look while its coordinating striped hat band adds style. The Rockit can be dressed up or down, making it a versatile and handsome hat

(1)
$72.00

…an 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…

$145.00

…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

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 2" Snap Brim   Made of: 100% Polypropylene   Comfort Sweatband Unlined Bailey

(1)
$66.00

Made in the USA The Bailey Guthrie is made of a new softening and finishing technology for Shantung Straw which creates an incredibly comfortable and flexible fit. As an added bonus, this is one of the few straw hats that is actually water resistant. The hat comes with the Dri-Lex moisture…

(3)
$130.00

…classic-width snap brim, traditional grosgrain ribbon trim and a Bailey staple side pin.   Ditch the plain straw fedoras this season and add a touch of personal style to your look with the Hartley Toyo Straw Fedora Hat by Bailey!    Approx. 3 7/8" Crown - Front 4 1/8" Crown -…

$82.50

…Introducing the Bailey Wait Sewn Braid Straw Pork Pie Hat. This is a great casual and flexible pork pie. It fits to your head and isn't stiff so you are able to shape it a bit to your liking.    Approx. 4" Telescope crown 1 1/2" Snap Brim   Made of: 50% Toyo Straw (Paper) 50%…

(3)
$80.00

…Tired of straw fedoras that crack or easily damage? The new Tate Braided Straw Fedora Hat by Bailey features its polypropylene "straw" that is braided and sewn for a lightweight and completely packable finish. Its classic fedora design features a pinch front crown accented with self hat band and a…

$66.00

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