All Products

  The Taxten by Bailey 1922 is a classic leather-paneled ivy cap with the casual appeal and presence of a true old-fashioned Sunday driving cap. On the interior, a finely woven grosgrain sweatband nicely accents custom Bailey lining, for a surprisingly rich experience. Continuing with this…

Related Products: Leather Ivy Cap | Leather Scally Caps | Bailey Poets Collection | Leather Newsboy Cap

  Made in the USA   Crafted in the USA of Bailey's superior fur felt blend, the new Ralat Superior Fur Felt Fedora Hat offers a classic pinch front crown and a stylish, wide brim. Trimmed with a Japanese grosgrain ribbon hat band and vintage flooring nail side detail, the Ralat…

Related Products: Rabbit Fur Fedora | Beaver Fedora | Gray Fedora | Black Wide Brim Fedora

  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: Summer Fedora | Cuban Hats | Straw Fedora | Bailey Straw Hats

  If you are an avid traveller and need a hat to match then the Packable Wheat Straw Sun Hat from Jeanne Simmons will be your companion. The 4-1/2" high cotton herringbone ribbon crown collapses when not worn, so it's perfect to pack flat in a suitcase. Braided wheat straw makes up the top of…

Related Products: Packable Sun Hats | Packable Travel Hats

  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: Crushable Straw | Raindura | White Straw Fedora | Packable 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 Fedora | Crushable Fedora | Blues

  Made in the USA   Introducing Bailey 1922’s Appley Elite Velour Wool Felt Fedora Hat, a true epitome of sophistication and American craftsmanship. Made with 100% wool felt, this hat showcases both luxury and warmth, making it a perfect addition to your fall or winter wardrobe.…

Related Products: Bailey Fedora

  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: 2 1 2 Brim Straw Fedora | Straw Hats Made In Usa | Small Head Hats | Bailey Straw Hats

  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: Palm Straw | Navy Straw

  A headwear piece that brings to mind abstract sculptures, there is no doubt that the Isabelle Sinamay Straw Fascinator Hat by Jeanne Simmons is a work of art. Constructed and shaped of sinamay straw, the disk base is asymmetrical and swirled which adds height and dimension. The sinamay straw…

Related Products: Black Fascinator | Fascinator

  Spice up any hat or hair style with the Suede Concho Hat and Headband from Jeanne Simmons! This versatile accessory can be affixed around a hat crown, ensuring that you'll be showing off your unique, trend-setting sense of style. Or wear it simply as a headband. The choice is yours!  …

Related Products: Hat Bands

  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: Small Brim Western Hats | Flat Brim Cowboy | Cowboy Hats | Flat Brim Western Hat

  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

  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 | Water Repellent Straw Hats | Black Straw Hats | Black Straw 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: Derby | Bowler | Bowler Derby | Bowler Hats

  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 | Bailey Western Hats | Leather Western Hats

  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: Flat Brim Fedora | Purple | Purple Fedora | Raw Edge Fedora

  Made in Mexico   Bailey presents the Shawnee 4X Toyo Straw Western Hat just in time for spring and summer! The Shawnee features a vent-woven crown for added ventilation offset with a dramatic, four-inch flared brim. Trimmings include a genuine leather band studded with silver-toned…

Related Products: Size 7 7/8 Cowboy Hat

  Just in time for spring, the Kids' Cherry Blossom Toyo Straw Sun Hat is a sweet new style from Jeanne Simmons. Featuring a classic sun hat design, this hat is detailed with bright red cherry blossoms embroidered along its brim. Flexible and packable, the Kid's Cherry Blossom Sun Hat is easy…

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

  Made in the USA Made in the USA, the Quil Shantung LiteStraw Open Crown Hat by Bailey is a shuntung straw hat that has been crafted using Bailey's exclusive LiteStraw® finish. A soft pebbled leather hat band adorns the crown and is a tasteful accent to the Quil. Features an open…

Related Products: Black Straw Hats | Open Crown | Dri Lex Sweatband | Water Repellent Straw Hats

  Be beautiful with the Campana Fascinator Hat from Jeanne Simmons! This gorgeous headband features satin ribbons, as well as feather accents with a mesh net veil, sure to be eye-catching. With this fascinator on your head, you'll always look stunning!   Approx. 3 7/8" Dish…

Related Products: Fascinator

  Classic and all-natural, the Crochet Seagrass Cloche Hat by Jeanne Simmons is the breathable straw hat you've been waiting for. Ideal for warm spring and summer days, the Seagrass Cloche is crocheted in a timeless bell-shaped cloche style and minimally adorned with a black grosgrain hat band…

  Handwoven in Ecuador, Finished in the USA   Accept nothing less than the best, like the Stansfield Panama Straw Fedora Hat from Bailey! This American-made hat is made of fine, reliable panama (toquila palm) straw, complete with a leather hat band and woven detail wrapping around…

Related Products: Stansfield | Panama | Fedora Made In Usa | Leather Fedora

  Thanks to the Chevron 4.5 Inch Brim Wheat Braid Lampshade Hat from Jeanne Simmons, the sun is absolutely no problem for you! Whether you're at the beach, on a walk, or just enjoying some time in the sun, the lampshade brim is perfect. Plus, it's hard to ignore the eye-catching grosgrain…

  This pin comes equipped with a straight pin and clip, so you can pin it onto a hat or wear it in your hair. Coordinate the flowers to match your outfit or mood!   Approx. 6" Diameter   Made of: 100% Polyester   Large Rose Metal Pin Metal Clip   Size:…

  The Noclin Leather Newsboy Cap by Bailey is crafted of smooth, soft-to-the-touch leather in a classic 8-panel newsboy design. Embellished only with a small Bailey side pin, the Noclin Newsboy is finished with a double-snap bill, grosgrain ribbon sweatband and quilted satin lining. Treat…

Related Products: Leather Newsboy Cap | 8 Panel Caps | Leather | Leather Caps

  Made in the USA   Elevate your style with Bailey 1922’s best-selling Tino Wool Litefelt® Trilby Fedora Hat. Handcrafted in the USA and made with the iconic and durable LiteFelt®, a treatment process on wool that makes it not only water repellant, but also retains its shape. A…

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