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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 (56)

Bailey Straw Hats

1 - 30 of 56 Products
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…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…

$70.00

…  Approx. 3 7/8" Crown 1 3/4" Brim   Made of: 55% Toyo Straw 45% Polyester    Self Hat Band Cotton Sweatband Bailey Side Pin OR Tag Unlined    *Due to different shipments from Bailey, hats may either have a Bailey pin or a Bailey tag on the hat band.*

$51.00

  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…

$55.25

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…

$93.50
Available Colors:
  • NATURAL

…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 is…

$90.00

…Fedora Hat by Bailey of Hollywood. Crafted in the USA of premium, fine-woven shantung straw, the Crase boasts Bailey's exclusive LiteStraw® finish which gives the hat its lightweight and incredibly supple feel in addition to making it shape retentive and water repellent. Never has a straw hat been…

$150.00
Available Colors:
  • NATURAL

…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 being weighed down by heavier straw, the Fernley has the…

$120.00

…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…

$115.00
Available Colors:
  • NATURALBLUE

…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 Straw (Cuenca Weave)   Woven Polyester…

$119.00
Available Colors:
  • NATURAL

  Combining toyo straw (paper) 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…

$51.00
Available Colors:
  • NATURAL
  • NAVYBLUE

  Made in Mexico Introducing the Bailey Jax 15x Straw Western Hat. This piece is simply gorgeous. There is a two-tone weave pattern from the crown to the brim. Also the crown is has a vented crown pattern that makes this piece stand out like no other. You simply can't go wrong with…

$90.00

…Introducing the Bailey Kace 10x Straw Western Hat. This piece almost looks like a lace pattern made out of straw from the crown all the way to the brim. It is a great look that stands out from your basic weave.   Approx. 4" Rodeo Crown 4 1/4" Brim Made of: 100% Straw

$75.00
Available Colors:
  • NATURAL

…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…

$60.00

straw hat is easy to wear. Stingy fedoras are quickly becoming a staple for anyone in the fashion know, and the Sydney is a confident straw shape to be enjoyed.   Approx. 4" C-Crown 1 1/2" Brim   Made of: 100% Genuine Panama Straw   Grosgrain Ribbon Hat Band Bailey

$127.50

…is the Bailey Thurman Center Dent Panama. This piece screams classic and casual what more could you ask for in a hat.   Approx. 4" Pinch Front Crown 2 3/8" Snap Brim   Made of: 100% Genuine Panama Straw (Brisa Weave)   Unlined Bailey Side Pin Grosgrain Hat Band …

$127.50

…flair, the Derian Toyo Straw Outback Hat by Bailey features their exclusive new Endura 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…

$100.00

…edge, the Rockett Toyo Straw Gambler Hat by Bailey features their exclusive new Endura 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…

$100.00
Available Colors:
  • TAN

…the Bailey Chaplin Panama Bowler 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)   Unlined Grosgrain Hat Band Bailey Side…

$150.00

…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%…

$59.50

…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:…

$55.25
Available Colors:
  • TANBROWN

…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 …

$60.00

…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 â  get the Guthrie 7X Shantung Straw Western Hat by Bailey today!    Approx. 4 1/8" - 4 1/4"…

$65.00
Available Colors:
  • IVORY

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 Straw   Inlaid Contrast 'Hat

$100.00
Available Colors:
  • NATURAL

…the Bailey of Hollywood Vito Toyo Straw Braid Trilby Fedora Hat which has a great combination of colors. The pattern on the crown creates the appearance of a hat band without one actually being present. This hat is also crushable so you don't have to worry about someone picking up the hat and…

$59.50

…  Introducing the Bailey Roll Up II Panama Straw Fedora Hat that can be rolled and placed into a bag for traveling. It is lightweight, comfortable and an all-around great find. Get the traditional Optimo crown Panama hat look with the Bailey Roll Up II Panama Fedora Hat!   Approx.…

$215.00
Available Colors:
  • NATURAL

…  Introducing the Bailey Vinton 20x Toyo Straw Western Hat. This is a great stiff cowboy hat. It has a gorgeous two-tone pattern from the crown to the brim. It also has a vent hole pattern throughout the crown to make sure you aren't uncomfortable in your hat. Approx. 4" Rodeo…

$100.00

…Introducing the Bailey Ryland 15x Toyo Straw Western Hat. This piece is created with a gorgeous cheveron pattern throughout the crown and brim to really make this hat stand out from the rest.    Approx. 4" Rodeo Crown 4 1/4" Brim Made of: 100% Toyo Straw (Paper) …

$90.00

…Made in Mexico  Introducing the Bailey Cassus 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…

$65.00
Available Colors:
  • NATURALTAN

  Made in Mexico    Introducing the Bailey Evers 10x Toyo Straw Western Hat. This is a great piece to keep you safe from the sun while enjoying something that you love. The crown has a vented hole pattern to make sure you are comfortable the whole time you are wearing it.  …

$75.00
Available Colors:
  • IVORY

Bailey Fields 4x Toyo Straw Western Hat. This piece is created with a two-tone pattern throughout the crown and the brim. Since this piece has a vented crown you can wear it out on the ranch and stay comfortable.   Approx. 4" Brick Crown 4 1/4" Brim   Made of: 100% Toyo Straw

$55.00
Available Colors:
  • NATURALTAN

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