All Products

  Please 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…

Related Products: Straw Trilby | White Straw Fedora | Short Crown Fedora | Black Straw Fedora

  Bailey introduces the Craig Polybraid Straw Fedora Hat, a new straw fedora for the spring and summer season. Crafted of packable polypropelene straw, the Craig Fedora is lightweight, packable (flexible) and water resistant. The Craig Fedora Hat is ideal for both men and women and is a great…

Related Products: Black Straw Fedora | Summer Fedora | White Fedora | Xxl Straw Fedora

  Please Note: This style no longer ships with a Bailey side pin. Instead, this style now has a small printed Bailey logo on the side bow.    Made in the USA The Tino Wool LiteFelt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines…

Related Products: Red Hats | Blues | Trilby | Hat Bands

  Please Note: This style fits towards the smaller end of its generalized letter size. See below or call us at 1-888-847-4287 for help with sizing. S = 6 3/4 M = 7 L = 7 1/4 XL = 7 1/2 XXL =7 3/4   Made in the USA Are you missing that one hat from your collection? I bet it…

Related Products: Derby | Bowler | Extra Large Size Hats Bowler | Bowler Xxl

  Made in the USA   Bailey's Guthrie 7X Shantung Straw Western Hat is made in the USA of high-quality, stiff 7X shantung straw in a classic cattleman design. Its lightweight design features a cattleman crown with three ventilation eyelets per side, a narrow two-ply grosgrain ribbon…

Related Products: Small Brim Western Hats | 3" Brim Western Hats | 3" Brim Western Straw Hats | Bailey Straw Hats

  Made in the USA The Briar Wool LiteFelt Fedora Hat is a great basic to have in your collection of hats. Featuring a safari-inspired design, the Briar adds a few stylish updates including a teardrop crown and handsome leather hat band. Great for both men and women, the Briar adds…

Related Products: Bailey Fedora | Packable Litefelt | Mens Felt Hats | Mens Hat Bands

  Featuring a soft and relaxed garment washed cotton twill construction, the LoPro Washed Cotton Strapback Baseball Cap by Otto is a comfortable, unstructured classic baseball cap. A low profile unstructured crown allows for a great fit and comfortable wear all day long. This baseball cap…

Related Products: Low Profile Fitted Baseball Caps | Dark Green | Extra Large Baseball Caps | Long Bill Cap

  Classic styling and skilled craftsmanship make the Bailey 1922 Salem Braided Fedora a style to be proud to own. The soft/packable sewn braid construction, center pinch crown, with striped grosgrain band of the Salem qualify this fedora as a carryover classic. This fantastic, unlined…

Related Products: Black Straw Hats | Straw Trilby | Xxl Straw Fedora | Packable Fedora

  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: Straw Fedora | White Fedora | Straw Stingy Brim | Bailey Fedora

  Made in the USA An excellent quality cattleman, the Lightning Wool and Angora Felt Cowboy Hat from Bailey is the classic cowboy hat. With its matching felt band and buckle, you too can be riding off into the sunset in the ultimate in American styling.   Approx. 4 3/4"…

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

  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 Mannes | Fedora | Bailey Fedora | Packable Fedora

  Made in the USA   Crafted with an extra wide brim and Bailey's Elite stiffened finish, the new Colver Elite Wool Felt Fedora Hat is a handsome new style for fall and winter. Starting with a classic teardrop crown, the Colver is trimmed with a narrow Japanese grosgrain hat band,…

Related Products: Winter Fedora | 3x Fedora | Blue Fedora | Xxxl Fedora

  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 Lang Elite Wool Felt Gambler Hat has a distinct teardrop crown, a mix of a telescope crown with a soft point. Bailey 1922 creates the elite…

Related Products: Telescope Crown | Gambler | Gambler Hat | Bailey Gambler

  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: White Trilby | Straw Fedora | Xxl Straw Fedora | Panama Hat Made In The Usa

  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: Ivy Cap Ear Flaps | Wool Newsboy | Caps With Ear Flaps | Plaid Flat Cap

  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: Packable Cowboy Hat | Crushable Straw | Outback Straw Hat

  Made in the USA   Dress to impress with the Pageant II 2X Wool Felt Western Hat by Bailey! Featuring a classic cattleman crown and dramatic flared brim, the Pageant II is crafted of genuine 2X wool felt. Trimmings are kept at a minimum for an elegant finish and include a self-felt…

Related Products: New Arrivals

  Made in Mexico    Introducing the Bailey Evers 10X Toyo Straw Western Hat. This is a great piece to keep you safe from the sun while enjoying something that you love. The crown has a vented pattern to make sure you are comfortable the whole time you are wearing it.    …

Related Products: Extra Large Cowboy Hats | Dri Lex Sweatband | Size 7 7/8 Cowboy Hat Straw | Straw Cowboy Hats

  Made in the USA   An excellent quality 4X virgin wool and imported angora felt blend, the Lightning Western from Bailey is the classic cowboy hat. With it's self felt hat band with buckle, you too can be riding off into the sunset in the ultimate in American styling.   …

Related Products: Extra Large Cowboy Hats | Small Brim Western Hats | Cowboy Hats | Size 7 7/8 Cowboy Hat

  Made in the USA   Charm and style are one, when it comes to the Bailey Brandt Lanolux Wool Felt Fedora Hat. You'll be walking tall with confidence in this center dent fedora with leather trim hat band!   Approx. 3 3/4" Center Pinch Crown 2 1/2" Downturned Brim   Made…

Related Products: Small Brim Fedora | 2 1/2" Brim | Leather Hats | Xxxl Fedora

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

  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

  Made in the USA   Handwoven, revolutionary yarn allows the Rothney Raindura Straw Fedora Hat by Bailey to be thermosetting! After being blocked into a handsome fedora silhouette, the Rothney is treated with a ultra-light water repellent coating. The end result being a durable hat…

Related Products: White Straw Fedora | Raindura | Crushable Straw | White Fedora

  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: Panama White Straw Hats | Derby | Bowler | Bowler Derby

  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…

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

  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: Optimo Straw | Black Straw Fedora | Brown Straw Fedora | Panama 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 | Blues | Packable Travel Hats | Safari

  Looking for something simple and casual? A quick grab when you are going for a walk around the neighborhood or challenging your friend to a game of tennis. A hat that is comfortable, adjustable, and to the point, the Cotton Twill Sport Visor is the perfect choice.   Approx. 2 1/2"…

Related Products: Visor