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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 (93)

Bailey Straw Hats

1 - 28 of 93 Products
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  Combining toyo straw 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 wear…

$75.00
Available Colors:
  • NATURAL

  Handwoven in Ecuador, Blocked & Finished in the USA   Bailey's panama straw hats, like the Giles Panama Straw Fedora Hat, are made from bleached leaves of the toquilla palm and handwoven in Ecuador. The multi-toned and spiral striped pattern body of the Giles is sure to impress.…

$225.00

…Please Note: Due to the nature of the straw, there may be some variance from hat to hat and is part of its beauty and uniqueness.   Made in the USA   The Braylon Sisal LiteStraw Fedora Hat by Bailey features a finer weave than most other straws in a classic design, perfect for…

$170.00
Available Colors:
  • BLACK
  • NATURAL

…USA   With the Racer Panama Straw Fedora Hat by Bailey you get both comfort and style. This is a custom panama handcrafted in Ecuador with a woven crochet teardrop crown and brisa snap brim. Finishing touches are the Japanese grosgrain ribbon hat band and finely woven sweatband. The Racer…

$225.00
Available Colors:
  • NATURAL

…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…

(6)
$170.00
Available Colors:
  • NATURALBLACK

…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

(2)
$80.00

…per side, a narrow two-ply grosgrain ribbon hat band tied at the side and a custom Bailey spur side pin. Stay cool and keep the sun out of your eyes with a quintessential western hat style – get the Guthrie 7X Shantung Straw Western Hat by Bailey today!    Approx. 4 1/8" - 4 1/4" Cattleman…

$110.00
Available Colors:
  • IVORY

…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…

(29)
$85.00

…flair, 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…

(2)
$135.00

…about the subtle details with the Ronit Toyo Straw Blend Trilby Fedora Hat by Bailey. The multi-colored braid adds dimension while the colorblocked grosgrain ribbon hat band adds contrast and interest. These finer details come together to a create a hat with effortless charm.   Approx. 3…

$80.00
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…

$63.75

…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 blocked and finished in the USA by master craftsmen. The resulting hat is lightweight, supple…

(2)
$220.00

  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…

$105.00
Available Colors:
  • NAVYBLUE
  • VANILLA
  • NATURAL

…on today's modern man.   Approx. 4" Center Pinch Crown 2" Snap Brim   Made of: 55% Toyo Straw 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 true…

$85.00

…Made in Mexico  Introducing the Bailey Cassius 7X Toyo Straw Western Hat. This piece has a great two tone pattern throughout the crown and brim. You can go from a day at the ranch to a evening at the rodeo without having to change your hat. The vented crown adds comfort and style so you…

(1)
$90.00
Available Colors:
  • NATURALTAN

…Made in Mexico   Bailey's Vaquero 10X Palm Straw Western Hat is a classic wide brimmed western hat made in Mexico of palm straw. With its cattleman crown and a wide shovel brim, the Vaquero is sure to make a statement wherever you go. Features a narrow leather hat band neatly secured by a…

$80.75
Available Colors:
  • BLACK

…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 teardrop crown and all-around snap stingy brim. A striped inlaid "hat band" adorns the…

(6)
$90.00

…for holding a golf pencil, and a Bailey micro side pin. Get out on the green in style this season with the Daxton Seagrass Straw Fedora Hat by Bailey!   Approx. 4" Tear Drop Crown 3 1/2" Upturned, Overwelt Brim   Made of: 100% Seagrass Straw   Made in the USA Wide…

$170.00
Available Colors:
  • SEAGRASS

…in Ecuador   Bailey's Bystrom Panama Straw Fedora Hat, made out of 100% toquilla palm leaves, has come to stand out. A leather cord hat band and a pop of contrasting color on the pinch front crown provides a unique and versatile style. A uniquely made Panama hat with a timeless look! …

$225.00
Available Colors:
  • TAWNY

…Further detailing includes a Bailey micro side pin and moisture-wicking sweatband. Can elegance be functional? Yes, with the Lachlan Raindura Straw Fedora Hat by Bailey!   Approx. 4 1/2" Tear Drop Crown 2 7/8" Flat Underwelt Brim   Made of: 63% Toyo Straw 37% Acrylic    …

$170.00
Available Colors:
  • MAUVE
  • TAN

…summer 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" Round Crown 2" Snap Brim   Made of: 100% Panama Straw (Toquilla Palm)…

(2)
$200.00
Available Colors:
  • BLEACH

…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"…

(1)
$220.00
Available Colors:
  • NATURAL

…Cuban Panama 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.

$220.00
Available Colors:
  • BLEACH

…size up.    Made in Mexico    Introducing the Bailey Fields 4X Toyo Straw Western Hat. This piece is created with a two-tone pattern throughout the crown and the brim. The vented crown makes for a comfortable hat, so you can wear it out on the ranch all day long.   …

(2)
$75.00
Available Colors:
  • NATURALTAN

…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…

$80.00

…Made in the USA Bailey's Winstone Raindura Straw Fedora Hat is the most shape retentive, durable straw hat on the market thanks to the exclusive Raindura® finish. This revolutionary process involves thermosetting yarn which has been handwoven inside a straw body. It is then blocked and…

$135.00
Available Colors:
  • BLACK
  • NATURAL

…of: 100% Genuine Panama Straw (Toquilla Palm)   Handwoven in Ecuador Blocked & Finished in the USA Lightweight Slightly Flexible Body Two-Tone Straw Body Twisted Front Dent - Crown Japanese Grosgrain Ribbon Hat Band Overwelt Brim Fine Woven Sweatband Bailey Crown Tip - Interior…

$225.00
Available Colors:
  • TAWNY
  • BLACK

…the Rockett Raindura Straw Gambler 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…

(3)
$140.00
Available Colors:
  • TAN

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