All Products

  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 brim that calls out to young headwear enthusiasts. This popular short snap-brim and teardrop crown are just perfect…

Related Products: Stingy Brim | Crushable Straw | Billy Braided

  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: 3xl Cowboy Hats | Xxxl Western Hats | Extra Large Cowboy Hats | Gus Crown

  Designed by Uncle Sam - well, not really, but if he did design a hat for the 4th of July, this would be it. Complete with a secret pocket inside the crown to stash away your ID, pocket change, or a copy of the Constitution. The Uncle Sam Mad Hatter Top Hat is a plush velvet top hat crafted…

Related Products: Uncle Sam Hat | Uncle Sam | Red White And Blue Hats | Red Hats

  Handwoven, Blocked, and Finished in Ecuador   The Panama Straw Grade, 10 Clasico Center Pinch Fedora Hat by Hats Montecristi is a beautiful hat made to last. This handwoven hat is grade 10, which indicates a fine weave giving it a flexible, soft, and supple feel. It features a…

Related Products: New Arrivals | Toquilla Straw | White Panama Hat | Panama Hat

  Made in the USA   Get ready for something new with the Melton LiteStraw® Seagrass Gambler Hat from Bailey! This unique hat is made with seagrass, a durable and stain-resilient material perfect for any stylish adventurer. No matter your plans, this hat should be your go-to! …

Related Products: Gambler Hat | Seagrass Gambler | Seagrass | Gambler

  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: Crushable Made In Usa | 3 1/2" Brim | Dri-lex Sweatband | Cattleman

  Please Note: This style features earflaps which may make the hat fit tighter when tucked into the crown. Please keep this in mind when ordering.  Made in the USA Introducing the Joe Eder Crushable Wool LiteFelt Earflap Western Hat by Bailey. This wool western hat is…

Related Products: Crushable Western Hats | Bailey Litefelt | Crushable With Earflaps | Crushable Wool Hats

  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

  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: Small Brim Western Hats | Womens Panama Hats

  Do you feel the need to impress at the annual 4th of July BBQ? Well the Giant Uncle Sam Top Hat is sure to make an impression. The 13" high flared crown has red and white vertical stripes with a base of white stars on a blue background. The colossal crown is supported by a 5" wide brim.…

Related Products: Red White And Blue Hats | Uncle Sam Hat | Uncle Sam

  Please Note: This piece fits a little loose. Please Note: This style features an aged and 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.   Made in the…

Related Products: Calvary Hat | Size 7 7/8 Cowboy Hat | 7 3 4 Cowboy Hat | Long Oval Cowboy Hats

  Made in the USA   Need an high-performance outdoor style that doesn't skimp on looks? The Redline Wool LiteFelt Safari Fedora Hat by Bailey features their proprietary wool Litefelt® that makes the Redline completely packable, crushable, and water resistant. This style is trimmed…

  Designed for those who thrive in the great outdoors and seek sun protection, Bailey's Dario Toyo Straw Blend Lifeguard Hat has an extra wide downturned brim perfect for keeping harmful rays off your face. The chin cord with adjustable toggle allows for extra security no matter the adventure.…

Related Products: Lifeguard Straw Hats | Extra Small Sun Hats | Size 8 Straw Hats | Extra Large Straw Lifeguard

  Made in the USA   The Dayton Raindura Outback Hat is part of Bailey's rugged Wind River® collection of western and outback styles. Made of toyo straw blend with a raindura finish, this is a revolutionary thermosetting yarn invented by Bailey. The Dayton is durable, shape retentive…

Related Products: Small Brim Straw Western Hats | Crushable Western Hats | Bailey Wind River | Crushable Straw

  Made in the USA   Bailey 1922 introduces their hybrid design of a traditional western with modern day style with the Niall Wool Felt Western Hat. The classic cowboy's cattleman crown is paired with a modern flat brim, mixing conventional with contemporary. The simple and narrow…

Related Products: Flat Brim Cowboy | Cowboy Hats | Flat Brim Western Hat | Cattleman

  Ye shiver me timbers! Y'arrr! Get ready for International Talk Like a Pirate Day (September 19th) with Elope's Scallywag Tricorn Hat. This structured tricorn has a textured polyester fabric with a pattern that mimics the patina leather retains from years of wear.    Approx. 6" High…

Related Products: Tricorn | Leather | Pirate Hat | Bicorn

  Handwoven in Ecuador, Finished in the USA Have you ever wanted to sport the style of the late and great Charlie Chaplin but didn't want to sweat through summer in a wool hat? Well now you don't have to. Introducing the Bailey Chaplin Panama Straw Bowler Hat with the heart of a…

Related Products: Charlie | Bowler Hats | Bowler | Derby

  Handwoven in Ecuador; Finished in the USA   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…

Related Products: Classic Fedora | Cuban Hats Panama | Panama Hat Made In The Usa | Straw Fedora

  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 | Travel | Bailey Litefelt | Blues

  Handwoven in Ecuador, Blocked & Finished in the USA   A classic panama with some funky color combinations, may we present the Cuban Panama Straw Fedora Hat by Bailey! Panama hats are a summer wardrobe staple but what makes the Cuban so unique is the two-toned Japanese grosgrain…

Related Products: Cuban Fedora | Straw Fedora | White Panama Hat | Panama Straw Hats

  The Octopus Pirate Hat by Elope features smooth faux leather on its outer panels with the left panel featuring an embossed octopus detail. Completing its stylish look, this pirate hat features matte faux suede on its inner panels and crown along with classic grosgrain ribbon trim along the…

Related Products: Tricorn Hats | Pirate Hat | Tricorn | Pirate

  Street-wise and ready for action, the Bailey 1922 Mannes Poly Braid Fedora Hat is one slick straw fedora, perfect for any scene or happening. This snap-brim braided straw hat is soft and packable for your convenience, but powerful and eye-grabbing in regards to looks and style.   …

Related Products: Bailey Crushable Fedora | Bailey Fedora | Trilby | Packable Trilby

  Made in the USA   May we present Bailey's Sterne Wool Felt Fedora Hat! This 3" stiff flat brim features a Japanese grosgrain ribbon hat band, braided cord overlay which has been secured in a fashionable knot. The raw edge brim is sharp and modern while the leather sweatband and…

Related Products: Flat Brim | Stiff Brim Fedora | Felt Fedora | Raw Edge Fedora

  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…

Related Products: Purple Fedora | Purple | Crushable Felt | Purple Hats

  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 | Polypropylene Fedora | Bailey Fedora | Bailey Straw

  Handwoven in Ecuador, Blocked & Finished in the USA   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…

Related Products: Panama | Optimo Crown | Roll Up Fedora | Gambler Or High Roller

  Please Note: The color 'Army Green' has a very strong brownish tint to it and appears more brown than green. 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…

Related Products: Curtis | Packable Hats | Curtis Wool | Traveler Fedora

  Made in the USA   Bailey 1922 debuts a new wool felt finish with the Croft Wool Felt Fedora Hat. Their 'beaver finish' creates a fuzzy and woolly texture. It has an 'outdoorsman' crown, a center pinch block with a wider center dent. The wide brim heightens the contemporary style,…

Related Products: Black Wide Brim Hats | Wide Brim Fedora | Beaver Fedora