All Products

  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 | White Fedora | Mens Summer Fedora | Bailey Fedora

  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 | Blue Straw Fedora | Trilby | Straw Stingy Brim

  UPF 50+ Sun Protection   No design is too much, that's why Kenny K has struck gold with the Two-Tone Toyo Straw Gambler Hat! This fashionable gambler features a zigzag striped weave that's so in style right now, as well as a grosgrain ribbon hat band and bow. Thanks to it's…

Related Products: Gambler Hat | Gambler Straw Hat | Two Tone Straw Hats | Gambler

  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 Straw Hats | 3" Brim Western Hats | Straw Cowboy

  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: Womens Wool Fedora | Packable Litefelt | Mens Fedora | Bailey Fedora

  Crafted of their exclusive fine toyolene braid, Bailey's Hooper Toyo Straw Blend Trilby Fedora Hat is not only incredibly breathable but also completely packable and crushable. Hooper features a color-blocked braided weave blocked into a teardrop crown and all-around snap stingy brim. A…

Related Products: Bailey Fedora | Packable Trilby | Straw Stingy Brim | Stingy Brim Straw 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 | Black Straw Hats | Toyo Straw Fedora | Toyo Straw

  No other flat cap is more distinctive than the oversized Newsboy Cap; Bailey's new Shawk Linen Newsboy Cap has the look! Made of lightweight and breathable linen, the Shawk Newsboy Cap features an oversized 8-panel crown and single-snap bill. The sole accent is a wooden Bailey side pin and…

Related Products: Linen Newsboy Cap | Linen Flat Cap | Lightweight Newsboy Cap | Bailey Newsboy

  UPF 50+ Sun Protection   Enjoy stellar UPF 50+ sun protection in a stylish hat crafted of hardy palm leaf straw. The Palm Leaf Straw Aussie Hat by Kenny K features a classic Aussie-inspired design complete with wide, downturned brim and handsome faux leather hat band. Three…

Related Products: Xl Straw Hats | Palm Straw | Palm Leaf Hat | Wide Brimmed Straw Hats

  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 | Bowler Xxl | Extra Large Size Hats Bowler

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Bogan Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an unbelievably…

Related Products: Bailey Fedora | 1 7/8” Brim | Wool Fedora | Snap Brim Fedora

  Made in the USA   Featuring Bailey's proprietary Elite Finish, the Winters Elite Wool Felt Fedora Hat boasts a luxuriously soft feel without the use of shellac. Innovated at the country's oldest hat factory in Adamstown, PA (since 1868), Bailey's Elite Finish creates an…

Related Products: 4 Inch Brim Fedora | Bailey Fedora | Blues | Brown Fedora

  Made in the USA   A stiff blocked pork pie hat from Bailey, the Walsh Polished Wide Brim Wool Felt Pork Pie Hat is a sharp addition to their already stellar line of headwear. This is a contemporary take on a classic pork pie with a wider brim and a flatter, telescope crown that…

Related Products: Wide Brim Pork Pie Hat | Pork Pie | Porkpie | Telescope Crown

  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

Handmade   The Tarpon Springs Floating Supplex Sailing Hat by Conner is an incredibly lightweight and completely crushable boating hat that also floats! Made of approximately 5 recycled plastic bottles, the Tarpon Springs Hat is eco-friendly in addition to all its great features. Fully…

Related Products: Sailing Hats | Floating Hats | Xxl | Crushable Hats

  UPF 50+ Sun Protection   The Pink Rose Raffia Straw Western Hat by Kenny K offers a romantic take on a classic straw western hat! Crafted with a classic teardrop crown and curved brim, the Pink Rose Raffia Straw Western is trimmed with a faux leather corset-style hat band…

Related Products: Extra Small Men Hats | Kenny K | Womens Summer Hats | Womens Hats Size Small

  Please Note: Sizing for this style runs one size small. Call us at 1-888-847-4287 for help with sizing.   UPF 50+ Sun Protection   The Star Spangled Toyo Straw Western Hat by Kenny K offers a patriotic take on a classic straw western hat! Crafted with a classic teardrop…

Related Products: 3x Large Cowboy Hats | Xxxl Hats | Womens Straw Hats | Xxxl Straw

  Please Note: The inner tags on this ball cap are mislabelled as L/XL. These caps are actually One Size and have an adjustable hook and loop strap at the back. The cap adjusts to fit adult sizes 7 (M) - 7 5/8 (XL).    UPF 50+ Sun Protection   Torrey UPF long bill cap is a…

Related Products: Long Bill Cap | Long Bill | Long Bill Baseball Cap | Torrey

  Made in the USA The Bailey Wynn LiteFelt Wool Fedora Hat is a simple yet elegant hat.  This hat has been factory treated and is water and stain resistant.   Approx. 3 7/8" Teardrop crown 1 1/2" Pre-Snap Brim (Front) 1" Curled Brim (Sides & Back)   Made of:…

Related Products: Trilby | Bailey Fedora | Trilby Hat | Pre-snap Brim

  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

  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: Bailey Fedora | Straw Fedora | Black Straw Hats | Polypropylene

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

  Please Note: The inner tags on this ball cap are mislabelled as L/XL. These caps are actually One Size and have an adjustable hook and loop strap at the back. The cap adjusts to fit adult sizes 7 (M) - 7 5/8 (XL).    UPF 50+ Sun Protection   Torrey UPF long bill cap is a…

Related Products: Long Bill Baseball Cap | Nylon Baseball Hat | Long Bill Hat | Long Bill Fitted Caps

  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 | Lightning | Size 7 7/8 Cowboy Hat | White Felt Hat

  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. The teardrop…

Related Products: Mannes | Xxl Fedora Hats | Packable Trilby | Braided Fedora

UPF 50+ Sun Protection   Handmade   The Bird and Feather Wool Felt Hat by Conner is a stylish and universally flattering shape with a little boho attitude. Handmade from 100% Australian wool felt, that provides UPF 50+ sun protection. Featuring a leather chin cord, Conner dove…

Related Products: Purple Hats | Wool Felt | Packable Felt Hat | Wool Floppy

  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 Curtis Wool LiteFelt Safari Fedora Hat is one of the most practical hats in the Bailey line. The classically designed safari fedora repels…

Related Products: Packable Hats | Wine Colored Hat | Black Crushable Fedora | Crushable

  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 | Chaplin | Derby | White Panama Hat