Bailey Trilby Hats

  Made in the USA   Bailey's Clorindon Elite Wool Felt Fedora Hat is a flexible fedora with a bubble crown and grosgrain ribbon trimmed brim. The crown features a wide Japanese grosgrain band which is overlaid with a silk blend, heathered, narrow ribbon, giving the Clorindon extra…

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…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…

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…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 stingy snap brim. Its easy-going,…

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…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 make the Giger an easy style to coordinate with while its classic grosgrain ribbon hat band…

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  Made in the USA   A classic pinch crown fedora hat with a few luxurious touches, the Flume Velour Fur Felt Fedora Hat by Bailey is a sumptuous new offering from Bailey 1922. Trimmed with a smooth leather hat band and removable black side feather, the Flume is simply breathtaking. A…

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…the USA   Scaling back and keeping it minimalistic and modern is Bailey's claim to fame with the Barksdale Polished Wool Felt Fedora Hat. The teardrop crown and hand curled brim have been designed with Bailey's Polished Elite Stiffened finish. The crown has been adorned with partial…

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…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, XL, and XXL; fits true to size.  

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…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 nail…

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…  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"…

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…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" Teardrop…

…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…

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…Ecuador; Finished in the 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…

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…Ecuador, the Hinx Hand-Dyed 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…

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…  A classic styled fedora by Bailey, the Ernest Elite Velour Wool Felt Fedora Hat. With a wide Japanese grosgrain ribbon hat band which has been finished with a single horizontal pleated tail. A dipped nail is strategically tucked behind, its a Bailey signature. And the Elite Velour finish…

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  Made in the USA   Part of Bailey's Poet® Travel Collection, the Boley Wool LiteFelt Roll Up Fedora Hat weighs in at 4 ounces and rolls up for easy on-the-go storage. Made in the USA using Bailey's exclusive wool LiteFelt®, the Boley is soft, packable/rollable and water repellent,…

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…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…

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…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…

…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…

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…The Japanese grosgrain ribbon hat band adds a subtle touch of texture while the interior boasts a comfortable cotton twill sweatband. Part of Bailey's Breed collection, the Mullan represents the brand's commitment to forward-thinking, creatively aesthetic hats.   Approx. 3 7/8" Center…

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  Made in the USA   Bailey Hat's most popular fedora. This premium wool felt is created with their exclusive blend of 100% virgin wool fibers, specially finished by their skilled craftsmen resulting in superior quality and unequaled value.   Approx. 4" Center Pinch Crown 2…

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…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 comfortable, you'll always be enjoying this hat! …

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  Made in the USA   Introducing Bailey 1922’s Appley Elite Velour Wool Felt Fedora Hat, a true epitome of sophistication and American craftsmanship. Made with 100% wool felt, this hat showcases both luxury and warmth, making it a perfect addition to your fall or winter wardrobe.…

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…  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 the Hernen…

…hat band that is extra long in order to be used to secure hat when rolled.     Approx. 4" Center Pinch Crown 2 7/8" Snap Brim   Made of: 100% Toyo Straw   Rollable Design - For Easy Packing Faux Leather Hat Band with Buckle - Extra Long To Secure Hat When Rolled Bailey…

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…  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 adding…

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…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. 3 3/4"…

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  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%…

…wool felt Ammon Wool Felt Teardrop Fedora Hat by Bailey is astonishingly silky to the touch. A classic teardrop crown (aka C-Crown) and all around downturned brim characterize this elegant fedora hat. Finished with a Japanese grosgrain hat band, small Bailey side pin, fine woven sweatband and fully…

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