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  Handwoven in Ecuador, Blocked & Finished in the USA   The Crispin Panama Straw Fedora Hat shows the craftmanship and care that goes into each design by Bailey! Adorned with only a braided leather hat band, the Crispin is anything but simple. The alternating weave in this…

Related Products: Navy Blue Straw Hats | Palm Straw | Montecristi Hats | Navy Straw

  Made in the USA   Bailey's Conlon Wool Felt Fedora Hat is our fall pick this year! The loose felt "beaver plush" finish makes for a unique look while the flexibility of the plush body makes the hat versatile. The brim has a slight curl and the crown is adorned with a narrow…

Related Products: Beaver Hat | Beaver | Beaver Fedora

  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: Crushable Straw | Packable Cowboy Hat | Small Brim Straw Western Hats | Outback Straw Hat

  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 | Wool Felt Fedora | Wide Brim Brown Fedora | Brown Fedora

  Made in Belgium   The soft, rich Matte Nappa Leather Ivy Cap by City Sport Caps will leave you looking polished and sophisticated. Known for its softness and durability, this nappa leather flat cap has flexible qualities making for a comfortable fit. Leather will always represent a…

Related Products: City | Leather Caps | Leather Newsboy Cap | Leather

  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 Hat With Chin Strap | Wool Felt | Dri-lex Sweatband | Bailey Western Hats

  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 | Panama Straw | Straw Fedora | Panama Hat Made In The Usa

  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: What Is Toyo Straw | All Weather Fedora | Breathable Straw Hats | Leather Hats

  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 Flat Cap | Linen Driving Cap | Linen Newsboy Cap | Linen Caps

  Introducing the Bailey Waits Sewn Braid Straw Pork Pie Hat. This is a great casual and flexible pork pie hat. It form fits to your head and isn't stiff, so it's very comfortable for all day wear.   Approx. 4" Telescope Crown 1 1/2" Snap Brim   Made of: 56% Toyo Straw 37%…

Related Products: Pork Pie | Waits | Pork Pie Hat | Crushable Pork Pie Hats

  FINAL SALE   Made in Belgium with Genuine Irish Virgin Wool Donegal Tweed   Village Hat Shop Exclusive   The Donegal Tweed Large Herringbone Newsboy Cap by City Sport Caps offers an old school look. Featuring a large distinctive black and white herringbone…

Related Products: Wool Tweed Newsboy Cap | Newsboy | Irish | City Sport Newsboy

  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 Derby | Extra Large Size Hats Bowler | Bowler | Derby

  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: Ivy Caps | Leather Newsboy Cap | Leather Caps | Suede Cap

  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 Hat | Open Crown | Open Crown Fedora | Crushable Felt

  Made in Mexico   Bailey's Vaquero 10X Palm Straw Western Hat is a classic wide brimmed western hat made in Mexico of palm straw. With its cattleman crown and a wide shovel brim, the Vaquero is sure to make a statement wherever you go. Features a narrow leather hat band neatly…

Related Products: Black Straw Cowboy Hat | Straw Cowboy Hats | Size 7 7/8 Cowboy Hat | Cattleman Crown

  Made in the USA   The Bailey Daxton Seagrass Straw Fedora Hat has arrived just in time for spring and summer! Featuring a lightweight and breathable seagrass straw build, the Daxton boasts a classic tear drop crown and slightly upturned brim. Details include a wide Japanese…

  Made in the USA   Part of Bailey's Wind River® collection of rugged hats, the Caliber Crushable Wool LiteFelt Western Hat features their exclusive LiteFelt® finish for added softness, water repellency and packability. The Caliber is crafted with a classic teardrop crown,…

Related Products: Packable Litefelt | Waxed Hats | Crushable Outback Hats | Crushable Western Hats

  Made in the USA   Striking and daring, the Nelles LiteFelt Wool Fedora Hat by Bailey is one of our favorites this season. Crafted from Bailey's signature LiteFelt wool, the Nelles is water repellent and shape retentive. A center pinch crown and turndown brim paint a beautiful…

Related Products: 2 1 2 Brim Fedora | Packable Litefelt | Crushable Felt | Fedora Made In Usa

  Made in Belgium   A City Sport Caps original, the Teflon™ Shield and Melange Wool Rollable Walking Rain Hat! Thanks to the Teflon™ fabric protection, this cap is made for long walks on a crisp autumn day. This rain hat is also wonderfully flexible, another plus for an on-the-go…

Related Products: Rain Hats

  It's always Shark Week when you're wearing the Great White Shark Jawesome Hat from Elope! It's the perfect fun hat for someone who's the life of any party they walk into, with a hidden interior pocket for all your secret sharky needs.   Approx. 10" Tall - Flat 12" Long - Flat …

Related Products: Shark | Jawesome | Hidden Pocket

  Made in Belgium with Genuine Irish Virgin Wool Donegal Tweed   Village Hat Shop Exclusive Say hello to the Herringbone Squares Donegal Tweed Wool Ivy Cap, one of City Sport Caps' newest additions to their already stellar line of flat caps. The Donegal Tweed…

  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: Bound Brim Fedora | Vintage Hats

  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 A classic outback style with a touch of western flair, the Derian Raindura Straw Outback Hat by Bailey features their exclusive new Raindura finish which helps the hat maintain its shape even after getting wet. Lightweight, pliable and completely packable, Derian…

Related Products: Outback Straw Hat | Straw Outback | Packable Cowboy Hat | Small Brim Western Hats

  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…

  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: Bailey Western Hats | Dri-lex Sweatband | Crushable Felt | Packable Litefelt

  Made in the USA   Bailey 1922 debuts a new style, the Walsden Wool Felt Homburg Hat, a modified homburg. The traditional center dent of the homburg has been grazed with two side dents, creating a center pinch crown. Bailey 1922 continues with modernization, by flattening the…

Related Products: Homburg | Homburg Hat Black | Pencil Brim | Homberg

  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 | Fur Felt Trilby | Snap Brim Fedora | Purple