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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 (57)

Bailey Fedora Straw Hats

1 - 30 of 57 Products
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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…

$110.00
Available Colors:
  • NATURAL

…  The Bailey Toyo Straw Fedora Hat is part of ále by Alessandra's new line for spring and summer. Featuring a classic fedora design adorned with a paisley bandana hat band, the Bailey has a unique look perfect for casual wear. Rest easy knowing you are protected not only by the hat's wide brim…

$68.00

  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…

$60.00
Available Colors:
  • NATURAL
  • NAVYBLUE

  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…

$65.00
Available Colors:
  • NATURAL
  • RED

  Handwoven in Ecuador, Finished in the USA   Introducing the Bailey Winnick Panama Straw Fedora Hat. The color and pattern on this hat is phenomenal. The mix of straw colors gives this hat life. It stands out amongst the rest and will be a great addition to any collection. …

$137.50
Available Colors:
  • DARKNATURAL

…color 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…

$70.00
Available Colors:
  • CHARCOAL

…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…

$90.00

…Lichter Toyo Straw Trilby Fedora Hat by Bailey features a striped design in a classic trilby fedora shape. Crafted of their famous toyo straw braid, the Lichter boasts a stiffer finish than their famous Billy and other similar styles. A self-straw hat band adorns the crown; a Bailey micro staple…

$70.00

…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

$65.00
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…

$70.00

…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

$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…

$70.00

…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…

$60.00

…The new Bailey Halsey Panama Straw & Suede Fedora Hat has a singular look that defies categorization. Handwoven with care by artisans in Ecuador, the Halsey boasts non-traditional suede leather embellishments for a uniquely rugged, outback-inspired look. A rich brown suede leather hat band…

$200.00
Available Colors:
  • NATURALOLIVE

…wide Japanese grosgrain ribbon hat band and small Bailey staple side pin; its super short (i.e. stingy) brim is upturned for maximum effect. One of a kind design in a stylish and modern shape, the Tor Short Panama Straw Trilby Fedora Hat is a genuine panama hat with contemporary flair.    …

$175.00
Available Colors:
  • BLACKNATURAL
  • NATURALBLACK

…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
Available Colors:
  • BLACKWHITE

…genuine panama fedora with a dash of color and 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.…

$160.00
Available Colors:
  • MULTI

…The Collonade Panama Straw Fedora Hat by Bailey combines a classic outback design and the hand-crafted artistry only a genuine panama straw hat can provide. Starting with a tear drop crown shape, the Collonade boasts a classic-width brim and a rugged natural leather bolo hat band. Perfect for those…

$140.00
Available Colors:
  • OLIVEGREEN

…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…

$160.00

…The Bailey of Hollywood Sydney Panama Straw Fedora Hat owns the summer with a strong straw weave that should stand the test of several Summers. Undeterred by the season's bright sun and general wear and tear, quality and style are heavily featured in this stingy brim genuine Panama fedora.

$150.00

…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)…

$70.00
Available Colors:
  • COPPER
  • BLACK
  • NAVYBLUE
  • SAND

  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"…

$67.50
Available Colors:
  • SMOKE
  • COFFEE

…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.…

$70.00
Available Colors:
  • FORESTGREEN

…  Bailey's unique Larsen Leather & Sisal Straw Fedora Hat boasts a singular design that combines lightweight sisal straw with smooth overlaid genuine leather. Crafted by expert Bailey craftsmen in the USA, the Larsen is simply breathtaking. A tonal side feather and Bailey staple pin…

$225.00
Available Colors:
  • NATURALBLACK

…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 along the crown's sides allow the hat to breathe while its singular upturned brim adds to the hat's unique…

$140.00

…  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. 4"…

$215.00
Available Colors:
  • NATURAL

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

straw in this style features black "staining" throughout. This is the intended look of the hat and does NOT constitute damage.    Handwoven in Ecuador; Finished in the USA   Looking for a panama hat with a bit more flair? The new Bailey Wasser Two-Tone Panama Straw Fedora Hat is…

$140.00
Available Colors:
  • BLACKNATURAL

  Introducing the Bailey Tennessee Fedora Hat. This is a great lightweight summer hat to keep you cool and protected from the sun at the same time. The brim and the crown are two different colors but the plaid hat band make them sync perfectly together. You can't go wrong with this piece.  …

$65.00
Available Colors:
  • TANBROWN

…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 Straw (Cuenca Weave)   Woven Polyester…

$140.00
Available Colors:
  • NATURAL

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