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 | Black Straw Fedora | Bailey Trilby

  Made in the USA Destined to be your new favorite outdoor hat, the Montana Wool Felt Campaign Hat by Bailey. Not just for park rangers, the Montana is a trendy headwear piece featuring a leather hat band with etched coordinates and a moisture wicking sweatband. Wonderfully…

Related Products: Campaign Hat | Montana Peak | Campaign | Montana

  The traditional 6-panel baseball cap has a fused buckram skeleton that forms the rounded athletic crown. Spandex has been woven into the brushed cotton twill baseball cap to allow for maximum stretch and comfort. Each panel has a tonal thread sewn eyelet for ventilation. The inner…

Related Products: Closed Back Baseball Caps | One Size Fits All | Cotton Fitted Cap | Flexfit Caps

  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: Summer Fedora | Black Straw Fedora | White Fedora | Womens Small Fedora

  A 6-panel, low profile fitted baseball cap is one of the most comfortable caps around. Spandex has been woven into the garment washed cotton crown enabling the baseball cap to stretch without disrupting the classic shape. The inner sweatband is also elasticized for an easy fit. There are 6…

Related Products: Low Profile Fitted Baseball Caps | Sized Baseball Caps | Closed Back Baseball Caps | Xxl Baseball Cap

  Please Note: This style no longer ships with a Bailey side pin. Instead, this style now has a small printed Bailey logo on the side bow.    Made in the USA The Tino Wool LiteFelt Trilby Fedora Hat from Bailey is a great looking hat at a great price! The hat combines…

Related Products: Wool Felt Fedora | Blues | Trilby | Basalt

  Made in the USA Introducing the Firehole Crushable Wool LiteFelt Western Hat by Bailey. Crafted with Bailey's exclusive LiteFelt® finish, the Firehole Western is not only incredibly soft and packable/crushable but also water repellent. Able to retain its shape, the Firehole is up…

Related Products: Bailey Western Hats | Beaver Hat | Crushable Western Hats | Small Brim Western Hats

  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: Stingy Brim | Grey Fedora | Small Brim Straw | Stingy Brim Straw Fedora

  A 6-panel, low profile fitted baseball cap is one of the most comfortable caps around. Spandex has been woven into the garment washed cotton crown enabling the baseball cap to stretch without disrupting the classic shape. The inner sweatband is also elasticized for an easy fit. There are 6…

Related Products: Low Profile Fitted Baseball Caps | Closed Back Baseball Caps | Low Crown | Fitted Baseball Caps

  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: Pork Pie Hat | Porkpie | Pork Pie | Telescope Crown

  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 Fedora | Fedora | Straw Trilby | Toyo Straw 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: Classic Fedora | Felt Fedora | Wool Felt Fedora | Brown Trilby

  The traditional 6 panel mid-profile baseball cap has a fused buckram skeleton that forms the rounded athletic crown. Spandex has been fused with the polyester calocks tricot (mesh) to allow for maximum stretch and comfort. Each panel has a tonal thread sewn eyelet for ventilation. The inner…

Related Products: Fitted Baseball Caps | Cap | Closed Back Baseball Caps | Sized Baseball Caps

  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 Flat Cap | Linen Newsboy | Linen | Linen Newsboy Cap

  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 | Extra Large Size Hats Bowler | White Bowler | Bowler Hats

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   A stunning piece by Toucan Collection that is also convenient, the Packable Toyo Straw Sun Hat. This hat is packable, which means it is the perfect travel companion. Features a…

Related Products: Sun Hats Made In Usa | Toucan Collection | Straw Hats Made In Usa | Usa Made Sun Hats

  The traditional 6 panel baseball cap has a fused buckram skeleton that forms the rounded athletic crown. Spandex has been woven into the cotton twill baseball cap to allow for maximum stretch and comfort. Each panel has a tonal thread sewn eyelet for ventilation. The inner elasticized…

Related Products: Fitted Baseball Caps | Fitted 6 3/4” Baseball Caps | Sized Baseball Caps | All Cotton Baseball Caps

  Made in the USA Introducing the Bailey Draper III Fur Felt Fedora Hat. For those that love their fur fedoras you can't go wrong with this piece and the gorgeous colors it comes in. The fur is a mix between rabbit and beaver and is soft to the touch.    Approx. 4 1/2"…

Related Products: Grey Fedora | Fur Felt Fedora | Brown | Stetson Beaver

  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: Waits | Pork Pie Hat | Straw Pork Pie | Pork Pie

  Made in the USA   The Dayton Raindura Toyo Straw 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…

Related Products: Crushable | Packable Cowboy Hat | Crushable Western Hats | Raindura

  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 | Pork Pie Hat | Straw Pork Pie Hats | Braided Porkpie Hat

  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: Safari Hat | Mens Rain Hats | Rain Hats | Bailey Fedora

  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 | Bailey Roll Up | Travel Straw Hats | Roll Up

  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: Bailey Crushable Fedora | Bailey Mannes | Poly Braid | Mannes

  Made in the USA   Bailey's Newhall Shantung LiteStraw Boater Hat is a modern take on classic Optimo and Boater hat styles made right here in the USA. Crafted of lightweight shantung straw with a firm finish, the Newhall features an optimo crown (tapered sides, round top with center…

Related Products: New Arrivals | Boater Hats | Straw Boater

  Made in the USA Another quality offering proudly crafted in the USA by experienced Bailey craftsmen! The Bailey 1922 Blixen Wool LiteFelt Fedora Hat is a classic felt fedora featuring a wide grosgrain hat band and sophisticated styling. Its exclusive LiteFelt® finish gives the hat…

Related Products: Hat Bands | Bailey Litefelt | Trilby | Navy Blue Fedora Hats

  Please Note: This is a handcrafted piece that takes 1-2 weeks to ship.   Made in the USA   Western just got chicer with Toucan Collection's Belted Southwest Wool Felt Gambler Hat! The ornate, multi-layered hat band is double-layered leather with multi-colored braided…

Related Products: Pencil Roll Brim | Gambler Hat | Gambler Or High Roller | Pencil Brim

  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 | Maroon Fedora | Usa Made Fedora | Bailey Fedora