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  FINAL SALE   Who says dressy can't be fun? The Kentucky Derby's Sazerac Mesh Swinger Hat is crafted of lightweight mesh and "straw" perfect for warm spring and summers months. A "straw" crown accented with a self hat band contrasts with its wide, asymmetric brim made of mesh with…

Related Products: Feather | Derby Hats | Derby | Wide Brimmed Straw Hats

  Made in Mexico   Presenting the Spear Point Wool Felt Rancher Fedora Hat from Charlie 1 Horse. With its raw edge brim and an eye-catching arrowhead crown detail, this hat harmoniously combines a classic look with contemporary style. The distressed fabric band and faux snakeskin…

Related Products: Charlie 1 Horse | Charlie 1 Horse Hats | Silverbelly Fedora | Charlie One Horse Hats

  Made in the USA  Made in the USA and part of their Frontier Collection, Bailey's Clayton Wool and Fur Felt Blend Gus Western Hat is all quality and tradition. With a traditional gus crown, this stiff western also features an expertly crafted pencil rolled brim. The finest wool…

Related Products: Pencil Curl Brim | Pencil Brim | Bailey Western Hats | Small Brim Western Hats Gus

  Made in the USA   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…

Related Products: White Fedora | White Wool Fedora | Wool Felt Fedora | Bailey Fedora

  Handwoven in Ecuador, Blocked & Finished in the USA   The Hurtle Panama Straw Fedora Hat is a unique piece by Bailey. Featuring a diamond crown that has been artfully ventilated, this genuine panama is headwear artistry at its finest. A Japanese grosgrain ribbon hat band and…

Related Products: Straw Fedora | Blue Straw Fedora | Black Straw Fedora | Panama Straw Hats

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Bogan Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably…

Related Products: Black Fedora | Bailey Fedora | Snap Brim Fedora | Stingy Brim

  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…

Related Products: Trilby | Fedora | Bailey Fedora | Black Straw Hats

  Made in the USA   Bring back those classic western vibes with the Chisolm Wool Litefelt Cattlemen Western Hat by Bailey. Part of their Wind River collection, this classic western features a beautiful crushable/packable water repellent wool felt body with a comfortable…

Related Products: Cattleman | Cattleman Crown | Bailey Western Hats | 3 1/2" Brim

  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,…

Related Products: Roll Up Fedora | Bailey Poet | Lightweight Fedora | Packable Litefelt

  Made in the USA   Bailey's Architect Fur Felt Cattleman Western Hat is the luxury experience in headwear. Crafted of superior fur felt, that you can keep in pristine condition thanks to the included hat brush. Handcrafted, this style takes a traditionally western silhouette with…

Related Products: Small Brim Western Hats | Small Brim Cowboy | Cattleman Crown | Cattleman

  Made in the USA Made in the USA, the Quil Shantung LiteStraw Open Crown Hat by Bailey is a shuntung straw hat that has been crafted using Bailey's exclusive LiteStraw® finish. A soft pebbled leather hat band adorns the crown and is a tasteful accent to the Quil. Features an open…

Related Products: Black Straw Hats | Open Crown | Flat Brim Straw | Dri Lex Sweatband

  Made in Mexico   The Stars and Stripes Straw Western Hat by Charlie 1 Horse touts a classic western hat shape outfitted with an aged, USA flag-inspired hat band. Featuring an aged finish with curved, wired shapeable brim, the Stars and Stripes Western is a great unisex western hat…

Related Products: Straw Cowboy Hats | Straw Hats Made In Usa | Usa Cowboy Hats | Straw Western

  Made in the USA   The 1890s slang word hightail originated from US cattle ranches, where many animals flee with their tail up. The Bailey Hightail Wool Felt Western Hat is made of a 2X wool felt firm/stiff body; it has a plaited cotton cord hat band, topped with a tricolor woven…

Related Products: Cowboy Hats | Dri-lex Sweatband | Bailey Western Hats | Chin Strap

  Made in Mexico   Charlie 1 Horse brings us a hat with character this spring/summer season, the Midnight Toker Shantung Straw Wide Brim Fedora Hat! Made in Mexico of 100% shantung straw, the Midnight Toker is adorned with a turquoise and ivory beaded hat band, suede tassels and an…

Related Products: Wide Brim Fedora | Charlie One Horse Hats | Suede Fedora | Charlie 1 Horse

  Handwoven in Ecuador, Blocked & Finished in the USA   Cousin Joe used to wear this hat as he wandered through the streets of the French Quarter back in the good old days of antediluvian New Orleans. Unbelievably, he rode out the storm with a supply of several 20-gallon jugs of…

Related Products: Straw Fedora | White Trilby | Panama Hat Made In The Usa | Fishing Hats

  Handwoven in Ecuador; Blocked & Finished in the USA   Bailey presents their Tully Plaid Panama Straw Western Hat, a striking new addition to their 1922 timeless collection. The Tully is a genuine Panama hat meticulously handwoven in Ecuador using 5 distinct straw hues for a…

Related Products: Extra Large Panama Hat

  Made in the USA   Make a statement with the Caprole Wool LiteFelt Walker Trilby Hat by Bailey 1922! The Caprole is a unique trilby that is water resistant, stain repellent, and shape retentive making it ideal for styling anywhere you go. It includes a removable side duck feather, a…

Related Products: Trilby | Feather | Humphrey Bogart | Walker

  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…

Related Products: Black Fedora | Gangster | Gangster Hat

  Bailey's Foster Herringbone Plaid Wool Earflap Newsboy Cap is a 8/4 cap made of a wool blend. Convertible earflaps make this the perfect option for a cold and windy day. An attractive herringbone pattern with contrasting stripes are the stand out detail. The Foster is fully lined making for…

Related Products: Newsboy Cap | Plaid Newsboy Cap | Flat Cap Ear Flaps | Ivy Cap Ear Flaps

  Elevate your winter ensemble with the sleek Elbin Plaid Fabric Ivy Cap by Bailey 1922. Designed with comfort in mind, this plaid patterned flat cap is crafted from a rayon-poly blend, features a cotton sweatband, and is fully lined. The close-fitting design and contour flat shape ensures a…

Related Products: Winter Flat Caps | Duckbill Caps

  Please Note: These fit a little snug from front to back so we recomment ordering 1 size up.    Made in Mexico    Introducing the Bailey Kace 10X Sisal Straw Western Hat. This piece almost looks like a lace pattern made out of sisal straw from the crown all the way to the…

Related Products: Extra Large Cowboy Hats | Orders | Straw Cowboy Hats | Size 7 7/8 Cowboy Hat

  Made in the USA   Introducing the Kilgore Raindura Toyo 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…

Related Products: Raindura | Wind Resistant | Bailey Wind River | Leather Hats

  Made in the USA   Bailey's Briles 2.0...the Brodnax Shapeable Open Crown Wool Felt Fedora Hat! Like the Briles, the Brodnax is an innovative hat that is shapeable. The open crown and brim is customizable, giving you countless looks in one hat. With the Brodnax, Bailey has added…

Related Products: Open Crown | Open Crown Hat | 5 Crown | Crushable Felt

  Made in the USA   The Bailey Darron Wool LiteFelt Pork Pie Hat is proudly made in the USA using their very own premium LiteFelt® finish for superior softness, flexibility, and repelling of water. Featuring the classic pork pie look including a telescope crown and stingy brim, the…

Related Products: Porkpie | Pork Pie Hat | Pork Pie Made In Usa | Pork Pie

  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,…

Related Products: Lightweight Fedora | Black Straw Fedora | Water Repellent Straw Hats | Black Straw Hats

  What do you take on your pizza? Topped with the works, Jacobson's Pizza Hat is deliciously pie-tastic! Wear it on National Pizza Day, February 9th, or just because! Who doesn't love pizza? As seen in the film, "Everything Everywhere All at Once".   Approx. 14” Diameter   …

Related Products: Tophat | Hat Sizer

  The Bailey Slater Fabric Ivy Cap adds a little bit of oomph to the standard flat cap style. The Slater features a contemporary five-panel design complete with single-snap bill and Bailey micro side pin. The sweatband and lining are lightweight for comfort and overall breathability. Ideal for…

Related Products: Summer Flat Caps | Basalt | Summer Driving Cap | Newsboy Hat Xxl

  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.…

Related Products: Bailey Fedora | Toyo | Toyo Straw | Blue Straw Fedora