All Products

    Made in the USA Bailey's Winstone Raindura Straw Fedora Hat is the most shape retentive, durable straw hat on the market thanks to the exclusive Raindura® finish. This revolutionary process involves thermosetting yarn which has been handwoven inside a straw body. It is then…

  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   The Curtis Wool LiteFelt Safari Fedora Hat is one of the most practical hats in the Bailey line. The classically designed safari fedora repels water and oil based spills. It is breathable, and durable and can be packed for ease of travel.    Approx. 4"…

Related Products: Blue Fedora | Bailey Litefelt | Blues | Bailey Fedora

  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: 2 1 2 Brim Straw Fedora | Bailey Fedora | Bailey Straw | Toyo

  A tasteful and elegent ivy cap from Bailey, the Liam Linen Cotton Ivy Cap! Made of linen and cotton blend, this hat features a subtle windowpane plaid pattern. A new Bailey favorite, especially with the finishing touches of a cotton twill sweatband and fully lined interior.    …

Related Products: Linen Caps | Linen Flat Cap | Linen Driving Cap

  A new staple for any flat cap fan, the Liam Linen Cotton Ivy Cap by Bailey! Made of a soft cotton and linen blend, this hat features a stripe pattern. Features a sewn bill, Bailey side pin, cotton twill sweatband and cloth lining.   Approx. 9 1/2" Front to Back, Flat 9 1/2" Side to…

Related Products: Linen Flat Cap | Flat | Linen Caps | Linen Ivy Caps

  Made in the USA Bailey's Winstone Raindura Straw Fedora Hat is the most shape retentive, durable straw hat on the market thanks to the exclusive Raindura® finish. This revolutionary process involves thermosetting yarn which has been handwoven inside a straw body. It is then…

Related Products: Crushable Straw | Packable | Water Resistant Fedora | Bailey Fedora

  Handwoven in Ecuador; Blocked & Finished in the USA   Introducing the Rene Two-Tone Panama 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…

Related Products: Two Tone Straw Hats | Panama | Bailey Fedora

  Charlie 1 Horse's stunning straw hats continue with the Lefty Palm Straw Fedora Hat. This custom designed hat features 100% palm straw, a braided hat band with tassels and an ornate concho accent. The semi-stiff structure of this fedora makes for a hat that will last and the center pinch…

Related Products: Straw Fedora | Hat | Charlie 1 Horse | Charlie One Horse Hats

  Calling all travelers, adventure-seekers, jetsetters, we 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…

Related Products: Gambler Or High Roller | Bucket Hats | Straw Bucket Hats | Xxxl Fedora

  Featuring a masculine distressed finish, the Lazar Suede Leather Ivy Cap is a deluxe flat cap by Bailey 1922. Crafted of genuine pig skin leather with a distressed suede finish, the Lazar is a distinctive cap for flat cap lovers. Four small panels comprise the back half of the cap while the…

Related Products: Bailey Poet | Leather Flat Cap | Ivy Caps | Leather Caps

  Bailey's Leif Linen Cotton Pub Cap is a buttery soft flat cap for warm weather thanks to the blend of linen and cotton. With a contour 8-panel shape, the Leif is designed to fit snugly. The stripe pattern completes this overall classic style.    Approx. 9 1/2" Front to Back - Flat…

Related Products: Linen Flat Cap | 8 Panel Caps

  Handwoven in Ecuador; Finished in the 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…

Related Products: Bailey Panama

  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: Humphrey Bogart | Trilby | Feather | Walker

  Handwoven in Ecuador; Blocked & Finished in the USA   Bailey's Moren Vented Panama Straw Western Hat is a genuine Panama straw hat handwoven in Ecuador then blocked and finished in the USA. Featuring geometric venting along its classic cattleman crown, the Moren is finished…

Related Products: Womens Panama Hats

  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 Felt Fedora | Bailey Fedora | White

  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 | Charlie One Horse Hats | Long Oval

  Made in the USA The Switchback is a classic Wind River® by Bailey western style. Made in the USA of their exclusive wool LiteFelt® that is both packable/crushable and water repellent, the Switchback features a braided leather hat band and curved brim for a timeless Aussie/western…

Related Products: Crushable Western Hats | Xxl Cowboy Hats | Leather Hat Bands | Bailey Wind River

  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

  Handwoven in Ecuador, Blocked & Finished in the USA   With the Racer Panama Straw Fedora Hat by Bailey you get both comfort and style. This is a custom panama handcrafted in Ecuador with a woven crochet teardrop crown and brisa snap brim. Finishing touches are the Japanese…

Related Products: Panama Trilby | Palm Straw | Lightweight Fedora | Panama Hat

  Made in Mexico   Bailey presents the Koslo II 15X Shantung Straw Western Hat just in time for warm weather! The Koslo features premium 15X shantung straw with a firm finish in a stylish two-tone weave. Its timeless cattleman crown features vent detailing and is finished with a…

  Made in the USA   The Godwin Elite Superine Velour Wool Felt Fedora features Bailey's newest finish, a wool velour. Designed with sustainability in mind, this finish is made to mimic the feel of fur felt but is made completely of wool. A buttery-soft genuine leather hat band with a…

Related Products: Purple Fedora | Purple | Flat Brim Fedora | Fur Felt Fedora

  Please Note: This style features an aged/burned/stained finish. This is the intended look of the hat and does NOT constitute damage. Please enlarge each thumbnail image for a close-up view of the aged and stained finish.   Go big or go home! That's what we say when it comes to the…

Related Products: Charlie One Horse | Gus Hats | Gus Straw Hats | Palm Straw Hats

  Made in the USA Introducing the Firehole Crushable Wool LiteFelt Western Hat by Bailey. Crafted with Bailey's exclusive LiteFelt® finish, the Firehole Western is not only incredibly soft and packable/crushable but also water repellent. Able to retain its shape, the Firehole is up…

Related Products: Firehole

  Made in Mexico   Bailey presents the Rausch 7X Jute Straw Western Hat just in time for summer! Featuring an airy jute straw weave, the Rausch is lightweight and incredibly breathable. Details include a shallow cattleman crown (center dent, pinched sides), vented detailing along the…

Related Products: New Arrivals

  Made in Mexico   Style and class combine for the Traveler Wool Felt Crossover Hat from Charlie 1 Horse. This wonderful hat features western-inspired styles in a druable wool felt body and the iconic Charlie 1 Horse branding. The narrow leather hat band wrapping around the crown has…

Related Products: Charlie 1 Horse Hats | Charlie 1 Horse | Silver Hat Bands | Band

  Made in Mexico   The Chisos Shantung Straw Fedora Hat from Charlie 1 Horse is a celebration of color and quality straw hats. Made in Mexico of 100% shantung straw, this fedora's satin scarf hat band steals the show. Featuring a multi-colored paisley pattern, the scarf has been…

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

  Made in the USA   The McCrae Wool Felt Gus Western Hat from Bailey features one of the most unique and oldest crown shapes in western headwear, the Gus crown. This crown was made famous by Robert Duvall's character in Lonesome Dove, Augustus McCrae, abbreviated to Gus. Made in the…

Related Products: Extra Large Cowboy Hats | Gus Crown | Gus Hats | Xxxl Western Hats