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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 (67)

Bailey Trilby Hats Straw

29 - 56 of 67 Products
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…Handwoven in Ecuador; Blocked & Finished in the USA   Featuring a stylized cuenca weave, the Alix Panama Straw Fedora Hat by Bailey is a distinctive new panama hat style for the season. Alix was handwoven in Ecuador then blocked and finished in the USA by expert artisans and craftsmen.…

$250.00
Available Colors:
  • BLACK
  • NATURAL
  • TAN

…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" Center Pinch Crown 2" - 2 1/8" Snap Brim   Made of: 100% Polypropylene   Grosgrain Hat Band Bailey Staple Side Pin Cotton Twill…

$85.00
Available Colors:
  • NATURAL
  • WHITE
  • BLACK
  • MOCHA

…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

…  Multi-colored with a unique patterned weave, the new Giger Panama Straw Fedora Hat will take your breath away. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert Bailey craftsmen, the Giger's striking good looks are no accident. The numerous hues…

(1)
$215.00

…2 3/8" Downturned Brim   Made of: 100% Panama Straw (Toquilla Palm) Cuenca Weave   Handwoven in Ecuador Blocked and Finished in the USA Panama Straw - Cuenca Weave Double Layer Japanese Grosgrain Ribbon Hat Band Bailey Side Pin Fine Woven Sweatband   Sizes: S, M, L,…

(1)
$200.00

…have just the hat for your on-the-go needs, Bailey's Balans Roll Up Toyo Straw Fedora Hat. Made from a toyo straw that has been crafted into an ultra-soft lightweight braid which can be rolled and packed to easily fit into a bag or suitcase. The Balans is finished with faux leather hat band that is…

$55.00
Available Colors:
  • CHARCOAL

…than the best, like the Stansfield Panama Straw Fedora Hat from Bailey! This American-made hat is crafted of fine, genuine 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"…

$170.00

hat look with the Bailey Roll Up II Panama Fedora Hat!   Approx. 4" Optimo Crown 2 1/2" Brim   Made of: 100% Panama Straw (Toquilla Palm) Brisa Weave   Handwoven in Ecuador Blocked & Finished in the USA Panama Straw - Brisa Weave Japanese Grosgrain Hat Band Bailey

(1)
$240.00
Available Colors:
  • NATURAL

…USA   Bailey's Ezra Vented Panama Straw Fedora Hat is a unique piece beautifully crafted with a ventilation pattern in the hat's crown. Trimmed with a distressed leather laced hat band and a removable side feather, this hat is handcrafted from 100% genuine panama straw.   Approx.…

$240.00
Available Colors:
  • NATURAL

Straw Fedora Hat, part of the Bailey Wind River® collection of outdoor styles. The Kilgore is crafted in the USA using Bailey's exclusive Raindura finish that makes the straw both water resistant and shape retentive. The Kilgore is lightweight and features a stylish patterned fabric hat band and…

(1)
$138.00
Available Colors:
  • TAN

Straw Fedora Hat by Bailey featuring a striking two-tone contrast weave. The Rene is artisanally handwoven in Ecuador then blocked and finished in the USA by expert Bailey craftsmen. The bold Rene boasts a genuine leather hat band complete with diagonal grosgrain side accent, black-dipped Bailey

$250.00
Available Colors:
  • BROWNBLACK
  • NATURALSILVER

…Panama Straw Fedora Hat by Bailey is a stunning hat featuring a hand-dyed body with a twist teardrop crown and snap brim. The front of the teardrop crown has an additional dent blocked by hand. Trimmed with a natural rope hat band to give it a pinch of ruggedness. Made of 100% genuine panama straw,

$225.00
Available Colors:
  • RUST

…Japanese grosgrain band, metal Bailey side pin, black-dipped signature Bailey nail accent, removable side feather, fine woven sweatband, and Bailey crown tip detail. Feel the breeze this spring and summer with the elegant Keats Vented Panama Straw Fedora Hat by Bailey!   Approx. 4" Center…

$240.00

…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

…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

…forward-thinking, creatively aesthetic hats.   Approx. 3 7/8" Center Pinch Crown 2 1/8" Downturned Brim   Made of: 50% Toyo Straw 50% Polypropylene   Packable/Crushable Multi-colored Straw Blend Design Japanese Grosgrain Ribbon Hat Band Bailey Logo Bar Underwelt Brim…

(1)
$100.00
Available Colors:
  • BLACK
  • SAND

  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…

$95.00
Available Colors:
  • BLACK
  • LATTE

…  The Phineas Two-Tone Panama Straw Fedora Hat is a new favorite from Bailey featuring genuine Panama straw which has been handwoven in Ecuador with leaves of toquilla palm. Its two-tone style is beautifully complimented by the Japanese grosgrain hat band, giving us a timeless look while…

$225.00

…USA   The Hernen Two-Tone Panama Straw Fedora Hat by Bailey has a unique two-tone weave throughout the hat, giving it a sophisticated and modern look. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert Bailey craftsmen. The striking good looks of…

$225.00

…have just the hat for your on-the-go needs, Bailey's Balans Roll Up Toyo Straw Fedora Hat. Made from a toyo straw that has been crafted into an ultra-soft lightweight braid which can be rolled and packed to easily fit into a bag or suitcase. The Balans is finished with faux leather hat band that is…

$100.00

  Kick back and relax with the Hester Toyo Straw Blend Fedora Hat from Bailey! This fedora features a cotton twill sweatband, as well as an unlined interior, making it one incredibly comfortable hat. Most notably, the grosgrain ribbon hat band has a stunning striped detail.   Approx.…

(1)
$100.00
Available Colors:
  • COPPER
  • SAND
  • GREEN

  Introducing the Bailey Mannesroe Poly Braid Straw Fedora Hat, it 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%…

(2)
$85.00

…  The Rask Gradient Panama Straw Fedora Hat by Bailey has been made using a gradation process that results in an awesome two-tone color meld. Woven by hand in Ecuador by skilled artisans then blocked and finished in the USA by expert Bailey craftsmen. The hat is trimmed with a Japanese…

$225.00
Available Colors:
  • BLACK
  • TAN

  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

…in the USA   The Imlay Knotted Shantung Straw Fedora Hat by Bailey has been created with a unique weave that adds texture to the body of this classic fedora. This style is simply decorated with partial suede hat band and Bailey's signature dipped nail. A finely woven sweatband provides…

$108.00
Available Colors:
  • NATURAL

…in the USA   The Imlay Knotted Shantung Straw Fedora Hat by Bailey has been created with a unique weave that adds texture to the body of this classic fedora. This style is simply decorated with partial suede hat band and Bailey's signature dipped nail. A finely woven sweatband provides…

$108.00
Available Colors:
  • TAN

…The Bailey Billy Braided Toyo Straw Fedora Hat is a top selling topper with a stingy brim that calls out to young headwear enthusiasts. This popular short snap-brim and teardrop crown are just perfect for a relaxed day or a night out on the town. A matching braided hat band and loop with the Bailey

$63.75

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