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Bailey Hats

Bailey of Hollywood. Bailey began producing fine dress headwear in 1922, priding itself on founder George Bailey's emphasis on the importance of a professionally crafted hat. Bailey has evolved from fine dress headwear to now include Outdoor Collections (Bailey Wind River) and Contemporary Hat Styles.

Bailey Hats are known for the craftsmanship of the product. The quality is apparent in all styles and fabrics including fur felt, leather, wool felt, Litefelt®, Panama straw, and cloth. Bailey Hats are durable; many of their hat products provide good protection in most weather conditions.

Staying true to its history of fine craftsmanship and detailing, the Bailey brand continues to evolve in design. Bailey features classic and contemporary styling.

DelMonico Hatter has a full collection of Bailey Hats and Caps. Select your style!

Bailey Vega Trapper Hat
Sale Price: $106.25    Price: $125.00

The Bailey Vega is a Trapper Hat offered in the Bailey Wind River collection for Autumn/Winter. Supple black leather and sleek black faux-fur update the traditional Trapper shape for a more conte ... Read more »
Bailey Harker Derby Hat
Sale Price: $93.50    Price: $110.00

The Bailey Harker Derby Hat- The Bailey Harker Hat is a handsome derby style hat in smooth brushed wool felt. The 1" super stingy brim turns up all around and is trimmed in a grosgrain ribbo ... Read more »
Bailey Parslow Trapper Hat
Sale Price: $63.75    Price: $75.00

The Bailey Parslow Trapper Hat is a comfortable trapper hat made from a Wool/Polyester blend. This classic hat features a melange pattern and is accented with antique copper hardware. The hat is ... Read more »
Bailey Madison Fur Felt Hat
Sale Price: $202.50    Price: $230.00

The Bailey Madison is a Classic Fur Felt Hat Handcrafted in the USA. This fully lined hat is fitted with a genuine leather sweatband and is delivered to you in a custom hat box. The center-dent c ... Read more »
Bailey Briar Hat
Sale Price: $76.50    Price: $90.00

Bailey Briar is a Litefelt(R) hat with a 3" down brim, teardrop crown, and leather hat band. Soft and packable, with memory, Litefelt(R) hats spring back to their original shape. Bailey use ... Read more »
Bailey Galvin Wool Newsboy Cap
Sale Price: $68.00    Price: $80.00

The Galvin Wool 8/4 Cap is an Italian-made larger bodied cap made up of several panels sewn together. The traditional 8/4 style cap has a press stud peak, enabling the crown to be worn up or down ... Read more »
Bailey Perry Hat
Sale Price: $102.00    Price: $120.00

Bailey Perry is included in the Bailey Casual Felt Hat Collection. The Perry has a 2" snap brim and a center-dent crown. Lavalee is made from Bailey Lanolux(R), which is 100% virgin wool w ... Read more »
Bailey Tino Litefelt Hat
Sale Price: $68.00    Price: $80.00

Bailey Tino Litefelt Hat is our Best Selling 100% Wool Felt Hat. The hat is soft, packable, and water repellent. The Tino has a 2" brim and a center dent crown. Feather is removable. ... Read more »
Bailey Cole Wool/Cashmere Ivy Cap
Sale Price: $80.75    Price: $95.00

The Bailey Cole Wool/Cashmere Ivy Cap is a beautiful Italian-made ivy style cap with classic lines and a soft, touchable wool/cashmere blend. The luxurious warm fabric is lined inside with smooth ... Read more »
Bailey Lord Wool Ivy Cap
Sale Price: $63.75    Price: $75.00

The Bailey Lord Classic Cap is Italian made with a soft wool feel. A press stud peak enables the crown to be worn up or to snap down into place, according to your liking. This hat comes fully lin ... Read more »
Bailey Riff Hat
Sale Price: $97.75    Price: $115.00

The Bailey Riff Hat is a classically styled center dent fedora made from polished Litefelt wool for a silky finish and a soft flexible feel. Comfortable and fashionable, this handsome hat has a 2 ... Read more »
Bailey Granard Aviator Hat
Sale Price: $159.80    Price: $188.00

The Bailey Granard is a vintage style leather trapper hat with a rounded paneled crown and a warm saddle brown color. Quilted canvas insets add a little texture and interest while the soft shearl ... Read more »
Bailey Hallam Cap
Sale Price: $96.05    Price: $113.00

The Bailey Hallam is a handsome leather flat cap with a center seam and paneled sides for a sleek close fit. Made from high quality smooth leather, this classic style cap will be a cool weather f ... Read more »
Bailey Turin Knit Hood
Sale Price: $59.50    Price: $70.00

The Bailey Turin Knit Hood is a modern style knit hood. Designed to keep your entire head warm, this soft lambswool blend hood is the perfect addition to your winter wardrobe! This hood extends d ... Read more »
Bailey Darron Hat
Sale Price: $70.55    Price: $83.00

Bailey Darron Telescope-Crown Hat - New from Bailey and Made in USA, Darron has a telescope crown and a 1 1/2" brim that can be snapped-down in the front or worn turned-up all the way-around ... Read more »
Bailey Derby Wool Felt Hat
Sale Price: $80.75    Price: $95.00

Derby Style Hat by Bailey. Premium Wool Felt Hat is made 100% Virgin Wool. Smooth felt finish with a 2 1/8" roll brim and binding on the edge of the brim. Hat is fully lined and has an inter ... Read more »
Bailey Litefelt Fedora
Sale Price: $76.50    Price: $90.00

The Litefelt Fedora is a 100% Wool Felt Water Repellent Hat. Litefelt hats are crushable and always spring back to their original shape. Fedora has a pinch crown and a 2 7/8" brim. Made in U ... Read more »
Bailey Lazar Cap
Sale Price: $68.00    Price: $80.00

The Bailey Lazar is a high quality 5 panel ivy style cap with a sleek profile and comfortable fit. Made from fine aged suede, this cap can be dressed up or down and always look good. ... Read more »
Bailey Brandt Downbrim Hat
Sale Price: $102.00    Price: $120.00

Bailey Brandt has a 2 1/2" brim worn turned-down all the way around. Crown is center-dent style. Brandt is made from Bailey Lanolux(R)- 100% virgin wool with a suede finish. After the ini ... Read more »
Bailey Bertram Litefelt Fedora Hat
Sale Price: $85.00    Price: $100.00

The Bailey Bertram Litefelt Fedora Hat is a handsome fedora with a severe front pinch for a crisp look. The 2 1/4 inch brim is a flattering width that looks good on almost anyone, and this brim c ... Read more »
Bailey Ike Wool Felt Trilby Hat
Sale Price: $51.00    Price: $60.00

The Bailey Ike Wool Felt Trilby is a short brimmed modern fedora with a snapped down 2 inch brim and curled up back for the distinctive trilby shape. The teardrop crown is ringed with a simple ba ... Read more »
Bailey Hollis Litefelt Derby Hat
Sale Price: $80.75    Price: $95.00

The Bailey Hollis Litefelt Derby Hat is a classic derby or "bowler" shaped hat with a rounded crown and short bound-edge 1 3/4 inch brim worn up all around. It is trimmed with a matchin ... Read more »
Bailey Inglis Litefelt Fedora
Sale Price: $80.75    Price: $95.00

The Bailey Inglis Litefelt Fedora is a clever modern fedora with a centerdent grad crown and wide unstructured 3 inch brim that slopes down in both front and back. Made from Litefelt, this hat is ... Read more »
Bailey Chipman Fedora
Sale Price: $80.75    Price: $95.00

The Bailey Chipman Fedora is a super versatile trilby fedora with a simple, sleek appeal. Unadorned by bands and feathers, this clean looking hat is made from soft, flexible Litefelt for a totall ... Read more »
Bailey Crowe Pork Pie Hat
Sale Price: $80.75    Price: $95.00

The Bailey Crowe Pork Pie Hat shows sometimes simple is best with a stripped down version of the classic pork pie hat. This jazzy style has a traditional telescope crown and modern 1 1/2 inch sti ... Read more »
Bailey Benny Cashlux Hat
Sale Price: $127.50    Price: $150.00

The Bailey Benny Cashlux Hat is a classy fedora with some special touches. The 2 1/4 inch snap brim features a double bound edge for an elegantly layered look. The crown has a low profile with a ... Read more »
Bailey Curtis Hat
Sale Price: $72.25    Price: $85.00

Bailey Curtis is a Litefelt(R) hat in the Casual Felt Hat Collection. The brim is 2 1/2" worn turned-down all the way-around. The crown has a low-profile and with a pinch. Bailey uses lea ... Read more »
Bailey Gangster Wool Felt Hat
Sale Price: $80.75    Price: $95.00

The Bailey Gangster is a 100% Wool Felt Hat. The hat has a 2 1/2" brim and a center dent crown. The feather shown is removable. The hat is fully lined and has an interior sweatband. Made in ... Read more »
Bailey Landis Hat
Sale Price: $233.75    Price: $275.00

The Bailey Landis is a soft high quality velour fur felt fedora with a low profile pinch front crown and a 2 1/2 inch turn down brim. Finished with a simple ribbon hat band, this hat is a sleek l ... Read more »
Bailey Cosgrove Hat
Sale Price: $106.25    Price: $125.00

The Bailey Cosgrove Hat is a modern take on the pork pie style hat. With an exaggerated 3 1/3" bound edge brim and a standard telescope crown, this hat has a truly unique look. Finished with a Ja ... Read more »
Bailey Galvin Tweed 8/4 Cap
Sale Price: $72.25    Price: $85.00

The Bailey Galvin Tweed cap is made in Italy in a Donegal Tweed pattern. This fully lined traditional 8/4 style hat has a press stud peak, enabling the crown to be worn up or down. The weave has ... Read more »
Bailey Garren Trapper Hat
Sale Price: $170.00    Price: $200.00

The Bailey Garren Trapper Hat is a sleek trapper hat made from a Genuine Pebbled Goat Leather. This hat is fully lined in a soft shearling fur for a comfortable and warm fit during the cold weath ... Read more »
Bailey Fur Porkpie Hat
Sale Price: $207.50    Price: $218.00

The Bailey Fur Felt Pork Pie Hat has a classic telescope crease in the crown. This hat has a small 1 3/8"" brim that can be snapped down or worn turned-up. The hat is fully lined and ha ... Read more »
Bailey Edsel Superior Fur Felt Fedora Hat
Sale Price: $276.25    Price: $325.00

The Bailey Edsel Superior Fur Felt Fedora is a handsome pinch front fedora with a slightly curled 2 inch brim for a vintage look and a simple ribbon hat band in the classic style. Made for modern ... Read more »
Bailey Obie Packable Wool Felt Hat
Sale Price: $93.50    Price: $110.00

The Bailey Obie Packable Wool Felt Hat is part of the Bailey Poet Collection- hats made for travel and exploration. The Obie is a softly blocked fedora with a centerdent crown and loose 2 3/8 inc ... Read more »
Bailey Wardell Lanolux Hat
Sale Price: $106.25    Price: $125.00

The Bailey Wardell Lanolux Hat is a casual downbrim hat with a lot of style. Made from Lanolux wool for a sueded finish and unique durability, this handsome hat has a centerdent crown and 2 5/8 i ... Read more »
Bailey Yates Hat
Sale Price: $76.50    Price: $90.00

Bailey Yates is a Litefelt(R) hat included in the Bailey Casual Felt Hat Collection. Bailey uses leading technology to produce Litefelt(R); a water repellent felt made of 100% wool. Soft and pa ... Read more »
Bailey Stockton Leather Ivy Cap
Sale Price: $89.25    Price: $105.00

Bailey Stockton Leather Ivy Style Cap included in the Bailey Casual Collection. Soft rich-feeling cap finished with a full satin lining. The cap is trimmed with a Bailey Pin on the left side. ... Read more »
Bailey Godfather Hat
Sale Price: $80.75    Price: $95.00

Bailey Godfather is a Wool Felt Classic Hat included in the Bailey Heritage Collection. The original name for the Godfather style hat was the Homburg. The Bailey Godfather has a 2 3/4" bri ... Read more »
Bailey Pelham Trapper Hat
Sale Price: $68.00    Price: $80.00

The Bailey Pelham Trapper Hat is a comfortable aviator style hat. This warm winter hat is made from a mix of wool and faux fur in a camo melange print. The earlaps on this hat can be buckled atop ... Read more »
Bailey Noble Superior Fur Felt Fedora Hat
Sale Price: $297.50    Price: $350.00

The Bailey Noble Superior Fur Felt Fedora Hat is a hand pinched diamond crown hat with a lot of room for individual shaping and style. The wider 2 7/8 inch brim lends the hat a vintage look, and ... Read more »
Bailey Berle Straw Fedora
Sale Price: $72.25    Price: $85.00

The Bailey Berle Straw Fedora is a handsome Toyo straw hat made with a unique blend of crochet and braid stitches to create an airy, open weave ideal for the hottest days of summer. The mesh crow ... Read more »
Bailey Billop Cap
Sale Price: $46.75    Price: $55.00

The Bailey Billop Cap is a contoured 5 panel cap made from a summer weight suiting fabric for a smart, sophisticated look. Light enough to dress up your warmest days, this cap has a subtle glen p ... Read more »
Bailey Birks Straw Baseball Cap
Price: $54.00

The Bailey Birks Straw Baseball Cap is a blend of military inspired design- with a flat, blocked crown and rounded front peak- and a traditional baseball cap style with a warm weather twist. Made ... Read more »
Bailey Blackburn Litestraw Fedora
Sale Price: $100.30    Price: $118.00

The Bailey Blackburn Litestraw Fedora is a fashionable fedora with a grad crown (sloped down slightly in both front and back) in a smooth, clean Litestraw tightly woven and completely waterproof. ... Read more »
Bailey Bren Litestraw Boater Hat
Sale Price: $85.00    Price: $100.00

The Bailey Bren Litestraw Boater Hat is a beautifully woven Bao Litestraw boater with tons of style. The weave is an intricate basketweave design just loose enough to allow a breeze to flow throu ... Read more »
Bailey Cudmore Panama/Leather Fedora
Sale Price: $233.75    Price: $275.00

The Bailey Cudmore Panama/Leather Fedora is a Western inspired hat with a beautifully matched mix of fabrics for a luxurious look. Expertly woven genuine panama straw- hand woven in Ecuador- form ... Read more »
Bailey Cunard Litestraw Fedora
Sale Price: $72.25    Price: $85.00

The Bailey Cunard Litestraw Fedora is a casual seagrass style fedora with a casual safari crown and wide 3 inch brim that slopes down in the front and back. An easy fit and open, airy weave give ... Read more »
Bailey Hemden Newsboy Cap
Sale Price: $46.75    Price: $55.00

The Bailey Hemden Newsboy Cap is a crisp, clean summer cap made from soft 100% cotton in the traditional newsboy paneled crown style. A slimmer fit and a carefully tailored silhouette give it a m ... Read more »
Bailey Inman Litestraw Porkpie Hat
Sale Price: $72.25    Price: $85.00

The Bailey Inman Litestraw Porkpie Hat is a flattering telescope crown porkpie hat made from flexible, water resistant Litestraw with a durable outer coating and smooth finish. Expertly woven wit ... Read more »
Bailey Jared Cap
Sale Price: $46.75    Price: $55.00

The Bailey Jared Cap is a classic flat cap with a smooth profile and sewn front peak to retain structure. Made from a summer weight cotton blend fabric, this cap is pre-washed for a comfortably f ... Read more »
Bailey Mogen Cap
Sale Price: $51.00    Price: $60.00

The Bailey Mogen Cap is a sleek, contoured cap with clever paneling to allow the closest most comfortable fit. 100% linen is patterned with subtle pinstripes and pre-faded for an easy casual look ... Read more »
Bailey Salter Genuine Panama Fedora
Sale Price: $233.75    Price: $275.00

The Bailey Salter Genuine Panama Fedora is a timeless classic made for summer. Grade 8 genuine panama straw is hand woven in Ecuador and hand blocked into shape in the USA to form a traditional t ... Read more »
Bailey Saynt Cap
Sale Price: $55.25    Price: $65.00

The Bailey Saynt Cap is a mix of traditional style and modern design; a 100% cotton summer weight cap in a classic ivy style with a flat crown and sleek silhouette, outfitted in a bold and fun fl ... Read more »
Bailey Telemannes Porkpie Hat
Sale Price: $55.25    Price: $65.00

The Bailey Telemannes Porkpie Hat uses the mixed colors of braided synthetic straw Bailey has made popular in other hats and forms them into a fashionable porkpie style hat for a whole new look t ... Read more »
Bailey Marken Flat Cap
Sale Price: $46.75    Price: $55.00

The Bailey Marken Flat Cap is a classic flat cap with a sleek close-fitting silhouette. The breezy 100% cotton fabric is printed with a cheerful gingham pattern for a great summer style. Lightly ... Read more »
Bailey Jessup Fedora
Sale Price: $89.25    Price: $105.00

The Bailey Jessup Fedora is a new, bold fashion statement for summer. Made from flexible, smoothly woven shantung Litestraw, this hat is water resistant and lightweight enough for the hottest day ... Read more »
Bailey Jarvis Straw Derby
Sale Price: $100.30    Price: $118.00

The Bailey Jarvis Straw Derby is a new, modern take on the traditional derby with a rounded crown and wider 2 3/8 inch flat brim for a look that is part bowler, part fedora, and all class. Shantu ... Read more »
Bailey Jett Pork Pie Hat
Sale Price: $80.75    Price: $95.00

Bailey Jett is a special hat for that special occassion. Bailey Jett is a wool felt hat with a silk finish. The crown is pork pie style trimmed with a matching grosgrain hat band. There is a sm ... Read more »
Bailey Wynn Hat
Sale Price: $70.55    Price: $83.00

Bailey Wynn is a Litefelt hat included in the Bailey Contemporary Collection. Litefelt hats are crushable, packable, water repellent and comfortable to wear. The Bailey Wynn has a 1 3/4 inch co ... Read more »