All Products

  Please Note: This hat boasts a floppy brim. This is the intended look of the hat.    Made in the USA   The Bailey Jackman Packable Wool LiteFelt Fedora Hat is a prime example of a casual unstructured hat. Think of Jed Clampett, Deliverance, 60’s Hippies. If you want look…

Related Products: Vegan Fedora | Grey Fedora | Packable Hats | Vegan Hats

  UPF 50+ Sun Protection   Prepare for sunny spring and summer days with the Wide Brim Toyo Straw Gambler Hat by Jeanne Simmons! Boasting the highest UPF sun protection rating possible (UPF 50+) with an extra wide brim, the Wide Brim Gambler has you (literally) covered from damaging…

Related Products: Wide Brimmed Straw Hats | Uv | Extra Wide Brim Hats | Wide Brim

  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: Orders | Dri Lex Sweatband | Extra Large Cowboy Hats | Straw Cowboy Hats

  This authentic hand-pressed Derby Hat (aka Bowler) is made of faux ultra-suede and features a distressed polyester band. Perfect for Victorian-inspired costumes or as the crowning finish to your steampunk costume.    Approx. 5 1/2" Round Crown 2" Curled Brim   Made of:…

Related Products: Bowler Hats | Derby | Bowler | Derby Hats

  Made in the USA Introducing the Roderick Wool Felt Western Hat by Bailey. The hat band is the true focal piece of this hat, the black leather hat band is decorated with a white stitching throughout the band. The side of the band is adorned with a little metal belt buckle to give…

Related Products: Extra Large Cowboy Hats | Black Western Hat | 7 3/4 Cowboy Hat | Size 7 7/8 Cowboy Hat

  Handwoven in Ecuador, Blocked & Finished in the USA   The Cutler is a most excellent and stylish Cuenca weave Panama. This beauty from Bailey is the perfect casual summer fedora. It comes complete with a stunning leather band and with Bailey embossed logo.     Approx.…

Related Products: Panama Straw Hats | Straw Fedora | Cuenca Weave | Panama Jack

  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 | Small Brim Straw Western Hats | Crushable Western Hats | Bailey Wind River

  Made in the USA   Featuring an elite finish, the 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…

Related Products: Winter Fedora | Blue Fedora | Bailey Fedora | Tan Fedora

  The George Washington Tricorn Hat by Elope is fit for any aspiring presidents out there! Featuring a black felt body, black grosgrain ribbon trim with a bow and faux silver button adornment strategically on the underbrim. This hat has a firm structure, sure to withstand any political speech…

Related Products: Tricorn Hats | Tricorn

  The Suede Pirate Hat by Elope you can embody famous pirates like Cheng I Sao or Grace O'Malley (if you don't know who these females are, we suggest a little Google sesh). This tricorn hat has a suede finish for luxury and to impress your fellow buccaneers. No swaping the deck, just a hearty…

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

  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: Gambler | Gambler Hat | Black Gambler Hat | Gambler Or Plantation

  With the Samantha Braided Toyo Straw Western Hat, Cappelli Straworld has taken practical design to the next level. With an ultra-lightweight body thanks to the semi-ventilated body, this is the perfect hat for a hot day at the beach or by the pool. Also stylish thanks to an alternating…

Related Products: Cowboy | Packable Cowboy Hat | Cowboy Hats | Chin Cord

  Combining toyo straw and thermo, the Bailey Elliot Straw Fedora Hat offers a breezy option for spring and summer. Lightweight and stylish, the Elliot features a pinch front crown, narrow grosgrain ribbon hat band and a stingy, pre-snapped brim. Don't sweat it this spring/summer, just wear…

Related Products: Straw Fedora | Summer Trilby | Cuban Hats | Summer

  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

  UPF 50+ Sun Protection   Perfect for a jaunt to the island off the coast of California that is this hats' namesake, the Catalina Toyo Straw Fedora Hat by Cappelli Straworld is made of a toyo straw blend with a braided and sewn design. Packable and crushable, it's perfect for little…

Related Products: Crushable Straw Hats | Wide Brim | Packable Sun Hats | Crushable Straw

  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: Extra Large Straw | Packable Fedora | White Straw Fedora | Raindura

  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%…

Related Products: Straw Fedora | Bailey Fedora

  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 | Small Brim Western Hats | Bailey Western | Dri-lex Sweatband

  Made in the USA   The Bailey Harker Wool Felt Bowler is possibly inspired by Jonathan Harker, one of the protagonists in Bram Stoker's Dracula. The jet nap finish on the wool felt modernizes this sleek derby sleek.   Approx. 4 1/4" Round Crown 1 1/2" Rolled Brim …

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

  Made in Mexico   Bailey's Costa Bangora Straw Western Hat is ready for summer - are you? Crafted of airy bangora straw with vent detailing along its crown, the Costa will help you stay easy breezy this season. Additional details include a two-ply grosgrain hat band with side ties,…

Related Products: New Arrivals

  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 | Straw Derby | Bowler Hats | Bowler

  The Rokit Toyo Straw Braid Trilby Fedora Hat by Bailey is great-looking, packable/crushable and lightweight. Its stylish color-blocked two-tone design gives this hat a unique look while its coordinating striped hat band adds style. The Rockit can be dressed up or down, making it a versatile…

Related Products: Summer Fedora | Trilby | Crushable Straw | Straw Fedora

  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: Pirate Hat | Bicorn | Tricorn | Tricorn Hats

  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: Optimo Crown | Rolled Panama Hat | Roll Up Fedora | Gambler Or High Roller

  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 | Bailey Panama Hat | Black Straw Fedora | Blue Straw Fedora

  Please Note: This piece fits a little loose. Made in the USA Introducing the Dynamite Wool Felt Western Hat by Bailey. This cowboy hat is equiped with a DRI-LEX® sweatband to make sure that if you are getting a little hot, your hat isn't going to show proof of that…

Related Products: Dri-lex Sweatband | Long Oval | Long Oval Cowboy Hats | Dri Lex Sweatband

  Made in the USA   The Bailey Guthrie is made of a new softening and finishing technology for Shantung Straw which creates an incredibly comfortable and flexible fit. As an added bonus, this is one of the few straw hats that is actually water resistant. The hat comes with the…

Related Products: Small Brim Straw | Small Head Fedora | Shantung Straw Hats | Small Head Hats

  Try out a more minimalist look with the Brune Houndstooth Wool Newboy Cap from Bailey. This reserved newsboy features a classic 8-panel crown, adorned only with a small Bailey metal logo bar. Furthermore, the sweatband is incredibly comfortable, like the smooth, soft interior lining. …

Related Products: Try On | Newsboy | Wool Flat Cap | Wool Cap