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: Crushable Straw | Straw Fedora | Bailey Billy | Cuban Hats

  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 | Straw Stingy Brim | Stingy Brim | Blue 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 | Mens Summer Fedora | White Fedora

  The Toucan Collection has something for everyone, including our vegan shoppers...introducing the Vegan Suede Safari Fedora Hat. With a suede finish but completely vegan, this hat has a handsome safari silhouette, perfect for fall. The only trimming is a braided faux leather hat band, also…

Related Products: Vegan Hats | Suede Fedora | Safari Fedora | Vegan Fedora

  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: Straw Trilby | Toyo Straw Fedora | Bailey Toyo | Packable Trilby

  Please Note: This style runs one size (1/8) too small. See below for fit or call us at 1-888-847-4287 for help with sizing.  6 3/4 = 6 5/8 6 7/8 = 6 3/4 7 = 6 7/8 7 1/8 = 7 7 1/4 = 7 1/8 7 3/8 = 7 1/4 7 1/2 = 7 3/8 7 5/8 = 7 1/2 7 3/4 = 7 5/8   Made in Mexico   Bailey…

Related Products: Extra Large Cowboy Hats | Size 7 7/8 Cowboy Hat | 8 1/2 Cowboy Hats | Cowboy Hats

  Made in the USA   UPF 50+ Sun Protection   The Turquoise Band Toyo Straw Gaucho Hat from the Toucan Collection, conjures up images of artistic Santa Fe, New Mexico. The wide brim gaucho style makes one think of the wild west, while the colorful multi-material hat band…

Related Products: Gaucho Hat | Sun Hats Made In Usa | Gaucho | Black Straw Hats

  Firm, structured, virtually impenetrable...the Bailey 1922 Dalton Cotton Blend Rain Safari Fedora Hat is an ideal find for wanderers and weather lovers everywhere. One of the premier water-resistant hats in the industry, the broad-brimmed Dalton is a rugged and rustic homage to the…

Related Products: Rain Hats | Cotton Fedora | Vegan Hats | All Weather Fedora

  Made in the USA   The Six Way Wool Felt Hat by Toucan Collection is so simple and chic, stripping everything back to celebrate the classic cloche style of the 1920s. The classic bell shape shines with no adornments to disrupt the seamless flow from crown to brim, also making it…

Related Products: Cloche X-large | Cloche | Packable Felt Hat | Wool Felt

  Introducing the Bailey Wait 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 | Straw Porkpie | Pork Pie Hat | Crushable Pork Pie Hats

  Celebrate a classic silhouette with Bailey's Carver Toyo Straw Blend Pork Pie Hat. Part of their spring/summer straw hat line, the Carver features classic details like a snap brim and telescope crown with a wide grosgrain ribbon and heathered thin ribbons stitched on top as a modern hat…

Related Products: Wide Brim Pork Pie Hat | Blue Straw | Summer Pork Pie Hats | Summer Hats

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   For the flower child in us all, the Velvet Rose Wool Beret by Toucan Collection is a beret with a beautifully adorned faux flower accent. Made of 100% wool, made of quality material…

Related Products: Wool Beret | Beret | Purple Beret

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   Toucan Collection's Toyo Straw Bow Cloche Hat is a unique and innovative design thanks to the straw bow that adorns the crown. A herringbone ribbon hat band adds a splash of color.…

Related Products: Toucan Hats | Red Hats | Straw Cloche

  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 | Black Straw Hats | Polypropylene | Beige Fedora

  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

  Bailey's Eli Two-Tone Vented Poly Braid Fedora Hat is a great hat for day excursions. Walk around town in this 2 1/2" brim dual colored braided fedora. The Eli features a grosgrain band with a color accent, and has a center dent that is flattering on all face shapes.    Approx. 4"…

Related Products: Blue Fedora

  Bailey presents the Marnix Waffle Five Panel Ivy Cap featuring a handsome waffled texture for a distinctive touch. The Marnix is a classic cut-and-sewn ivy cap boasting a contemporary 5-panel design and sewn bill. Accoutrements include a Bailey micro side pin, lightweight fabric sweatband,…

  Fashion need not be so flashy, and the Graham Cotton Blend Ivy Cap epitomizes that adage with a flash of brilliance! The Graham Ivy has the classic profile of a cap, with the crown stitched to the bill, it reinforces a strong and sleek silhouette. Carefully crafted from water resistant…

Related Products: Cotton Flat Cap | Bailey Caps | Bailey Ivy Caps | Cotton Driving Cap

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   Hailing from New York, the Toucan Collection is coming to us with the Camelia Wool Felt Cloche that reminds us of the roaring twenties and a time when NYC was the center of…

Related Products: Cloche | Wool

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   The Saddle Stitch Rose Profile Wool Felt Cloche Hat by Toucan Collection creates that magical moment when the leaves start to change color and the chilly air starts to make its way…

  The Denney Toyo Straw Blend Fedora Hat from Bailey is simple, with just a touch of flair! By flair, we're referring to the thin leather hat band wrapping around the crown, which nicely compliments the wide grosgrain ribbon hat band layered beneath it. The cotton twill sweatband is so…

Related Products: Black Straw Fedora | Small Size Straw Hats | Snap Brim Straw Hats