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 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 Sydney Panama Hat
Sale Price: $99.95    Price: $118.00

Bailey Sydney is a Genuine Panama Hat hand-woven in Ecuador and finished in the USA. Sydney; included in the Bailey Causal Straw hat Collection comes in several colors. The hat has a teardrop c ... Read more »
Bailey Cutler Panama Hat
Price: $107.50

Bailey Cutler is a soft 100% Genuine Panama Hat hand-woven in Ecuador with a center-dent pinch, graduated crown and a 2 7/8" pre-snapped brim. The Cutler has a tooled leather hat band and a ... Read more »
Bailey Brooks Panama Hat
Price: $107.50

Bailey Brooks is a Genuine Panama Hat with a teardrop crown and a 2" downbrim. Brooks has a grosgrain hat band and an interior sweatband. This hat has a heavier body. Hand-woven in Ecuador a ... Read more »
Bailey Spencer Litestraw Hat
Sale Price: $58.95    Price: $70.00

Bailey Spencer is a Litestraw(R) hat included in the Bailey Casual Straw Collection. Crown on this hat is teardrop style. The 2 3/8" casual brim can be worn turned-down all the way around. ... Read more »
Bailey Billy Packable Hat
Sale Price: $55.00    Price: $60.00

Bailey Billy has a teardrop crown and a stingy 1 3/4" brim that is snapped-down in the front. It is a soft, flexible braid hat with a matching braid hat band and an interior sweatband inclu ... Read more »
Bailey Mannes Hat
Sale Price: $55.00    Price: $60.00

Bailey Mannes is a multi-colored braid straw hat with a textured hat band that goes well with the color of the hat. The low c-crown shape measures 3 3/4"; it has a pinch. Bailey Mannes has ... Read more »
Bailey Lakewood Genuine Panama Hat
Sale Price: $119.95    Price: $130.00

The Bailey Lakewood Genuine Panama Hat is a handsome 100% genuine panama straw hat with a mixed taupe/lake color scheme that is truly unique. Woven in a Hamaca/Cuenca weave pattern for depth and ... Read more »
Bailey Miles Hat
Sale Price: $74.95    Price: $80.00

The Bailey Miles Hat is a classic pork pie crown hat woven from lightweight Bao straw. The weave on this hat is especially complex and beautiful, with a textured design and slight ventilation for ... Read more »
Bailey Johnny Straw Braid Hat
Sale Price: $57.50    Price: $63.00

Bailey Johnny is a Straw Braid Porkpie Style Hat. The Johnny is flexible and packable. The brim on this hat is 1 3/8" and is worn snapped-down in the front or turned-up all the way around. C ... Read more »
Bailey Monroe Packable Hat
Price: $53.00

Monroe is included in the Bailey Casual Straw Hat Collection. Bailey Monroe is made from a soft, flexible braid that is comfortable to wear. Hat is two-toned; crown is Ivory with a collection o ... Read more »
Bailey Salem Packable Hat
Price: $57.50

The Bailey Salem Hat is a classic braid fedora with a center dent crown and 2 inch snap brim. Flexible and soft, this hat is finished with a bright striped band for a cheerful and elegant summert ... Read more »
Bailey Tennessee Straw Fedora
Sale Price: $59.95    Price: $65.00

Bailey Tennessee is included in the Bailey Casual Straw Hat Collection. Hat is made from a very lightweight quay straw. Crown is pinch-front and the 1 3/4" brim is pre-snapped to be turned ... Read more »
Bailey Taxten Ivy Cap
Sale Price: $79.95    Price: $80.00

Bailey Taxten is a 100% sheepskin leather cap. Taxten is Ivy Style and is constructed of individual panels. Leather is a handsome weathered Brown. There is a small Bailey pin on the left-rear ... Read more »
Bailey Stockton Leather Ivy Cap
Sale Price: $89.95    Price: $95.00

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 Noclin Leather 8/4 Cap
Sale Price: $99.95    Price: $105.00

Bailey Noclin Leather 8/4 Style Cap included in the Bailey Casual Collection. Genuine leather with a full satin lining. ... Read more »
Bailey Cole Cashmere/Wool Ivy Style Cap
Sale Price: $78.95    Price: $88.00

Bailey Cole Cashmere and Wool Blend Ivy Style Cap- 50% Cashmere and 50% Wool blend. Handsome, comfortable fitting cap with a full-cut back and a full satin lining. Trimmed with an Oval Bailey Pi ... Read more »
Bailey Godfather Hat
Sale Price: $82.50    Price: $90.00

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 Perry Hat
Sale Price: $107.50    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 Brandt Downbrim Hat
Sale Price: $107.50    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 Galvin Wool Newsboy Cap
Sale Price: $69.95    Price: $73.00

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 Briar Hat
Sale Price: $72.95    Price: $85.00

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 Curtis Hat
Sale Price: $69.95    Price: $80.00

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 Yates Hat
Sale Price: $78.95    Price: $88.00

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 English Derby
Sale Price: $202.50    Price: $225.00

Bailey English Derby is a fur felt hat with a stingy rolled brim. The crown is derby/bowler style, fully lined and trimmed with a grosgrain hat band. This hat was a standout on the runways. Th ... Read more »
Bailey Wynn Hat
Sale Price: $69.95    Price: $78.00

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 »
Bailey Jamison Hat
Sale Price: $63.95    Price: $78.00

Bailey Jamison is a Litefelt hat included in the Bailey Contemporary Collection. Litefelt hats are crushable, packable, water repellent and comfortable to wear. The Bailey Jamison has a small 1 ... Read more »
Bailey Darron Hat
Sale Price: $69.95    Price: $78.00

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 Jett Pork Pie Hat
Sale Price: $79.95    Price: $88.00

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 s ... Read more »
Bailey Dalton Safari Hat
Sale Price: $44.95    Price: $55.00

Bailey Dalton is a water repellent hat. Dalton has a pinch crown, a 2 5/8" brim that is worn turned-down all the way around, and a leather hat band. Included in the Bailey Windriver(R) Col ... Read more »
Bailey Vega Trapper Hat
Sale Price: $98.95    Price: $113.00

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 »
St. Patrick's Day Derby Hat
Price: $75.00

We have specially ordered some good-quality, wool felt green derbies for the St. Patrick's Day festivities. Whether for your lodge party, a parade gathering, or anything else, this derby will be ... Read more »
Bailey Charlie Porkpie Hat
Sale Price: $55.00    Price: $62.00

Bailey Charlie is a Straw Braid Porkpie Style Hat. The Charlie is flexible and packable with a 1 3/8" brim and is worn snapped-down in the front or turned-up all the way around. Comfortable ... Read more »
Bailey Graham Cap
Sale Price: $38.95    Price: $45.00

Bailey Graham is a full-shaped cap with a leather tab at the back. Color shown is Tan. Graham is in the Bailey Windriver(R) Collection; a great hat to wear in all weather conditions. ... Read more »
Bailey Ice Wool Felt Top Hat
Sale Price: $81.95    Price: $90.00

The Bailey Ice is a wool felt Top Hat included in the Bailey Heritage Collection. The Ice has a 5" Tall Crown and a 2 1/8" Roll Brim. The brim is bound on the edge with a coordinating b ... Read more »
Bailey Gangster Wool Felt Hat
Sale Price: $79.95    Price: $90.00

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 Tino Litefelt Hat
Sale Price: $62.50    Price: $75.00

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 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 Duke Fur Felt Hat
Sale Price: $175.00    Price: $195.00

Bailey Duke is a fur felt classic hat with a small 1 1/2" brim that is worn snapped down in the front. Bailey Duke has a center crease crown, is fully lined and has an interior leather swea ... Read more »
Bailey Ferris Cap
Sale Price: $37.95    Price: $55.00

The Bailey Ferris cap is a rich tweed cap. The Ferris has a contour peak sewn to the cap body for shape retention and is sewn from four individual panels. Included in the Bailey Casual collection ... Read more »
Bailey New Yorker Hat
Sale Price: $81.95    Price: $90.00

Bailey New Yorker Fedora Hat- Long a mainstay in the Bailey Heritage Collection. Calls to mind classic elegance, Mad Men, and Old Hollywood style. Wool felt fedora with a 1 7/8" brim that is ... Read more »
Bailey Barr Hat
Sale Price: $97.50    Price: $110.00

The Bailey Barr Felt Hat has a center dent crown and a 2" Brim. Made of 100% Virgin Wool with a unique suede finish; lightweight, packable, and luxurious. The hat has a matching grosgrain ha ... Read more »
Bailey Fairbanks Hat
Sale Price: $68.95    Price: $78.00

The Bailey Fairbanks is an outdoorsy shape in water-resistant, 100% Wool Felt. Large sizes rest easy- this hat has the feature of coming in XXXL! (Comes in smaller sizes, too, of course.) Soft, p ... Read more »
Bailey Litefelt Fedora
Sale Price: $72.95    Price: $80.00

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 Lord Wool Ivy Cap
Sale Price: $56.95    Price: $63.00

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 Tweed Trilby
Sale Price: $79.95    Price: $94.00

The Bailey Tweed Trilby is returning for the Fall/Winter season in the Bailey Italian Collection. An updated version of a traditional shape. Hat is a wool blend, crafted in Italy with a full lini ... Read more »
Bailey Lord Nailhead Tweed Cap
Sale Price: $62.95    Price: $70.00

The Bailey Lord Nailhead Tweed Cap is an Italian-made cap with a soft, wool feel. Nailhead tweed is a unique offering that combines flecks of contrasting shades of a single color to create a rich ... Read more »
Bailey Augustin Fur Felt Velour Fedora Hat
Price: $169.00

Bailey Augustin Fur Felt Velour Fedora Hat - Soft velour finish, teardrop crown, 1 1/2" stingy brim. Genuine fur felt hat trimmed with a grosgrain hat band. Full satin lining and interior ... Read more »
Bailey Suntino Straw Fedora Hat
Sale Price: $62.95    Price: $70.00

The Bailey Suntino is a classic shaped Toyo straw fedora with a center crease crown and 2" brim that snaps down in front. Lightweight and soft, this versatile hat comes in a variety of rich ... Read more »
Bailey Lamar Straw Porkpie Hat
Sale Price: $63.95    Price: $70.00

The Bailey Lamar is a traditional pork pie style hat with a twist. The lightweight soft straw braid curves around the classic telescope crown while the modern stingy 1 1/2" brim can be worn ... Read more »
Bailey Carnegie Panama Hat
Sale Price: $105.00    Price: $120.00

Bailey Carnegie is a Genuine Panama hat hand-woven in Ecuador and finished in the USA. The Carnegie has a center-dent crown and a 2 3/8" brim. The band on this hat is a handsome two-tone m ... Read more »
Bailey Derby Wool Felt Hat
Sale Price: $81.95    Price: $90.00

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 Galvin Tweed 8/4 Cap
Sale Price: $69.95    Price: $75.00

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 Guthrie Litestraw Hat
Sale Price: $89.95    Price: $103.00

Bailey Guthrie is a soft and supple Litestraw(R) hat. Straw material is Shantung. Hat has a teardrop crown and a 2" brim that is snapped-down at the front. Bailey Guthrie has a comfortabl ... Read more »
Bailey Lord Ivy Style Herringbone Cap
Sale Price: $62.95    Price: $68.00

Italian made, with a soft wool feel. This Bailey Ivy Style Cap is available in a traditional herringbone tweed. Colors are Black Herringbone and Brown Herringbone. This cap comes fully lined with ... Read more »
Bailey Nichols Straw Fedora
Sale Price: $69.95    Price: $90.00

The Bailey Nichols is a fedora style Litestraw hat with a teardrop crown and 3" brim. The ventilated crown has a decorative diamond design, and the band is a layered fabric-and-leather hat b ... Read more »
Bailey Harker Derby Hat
Sale Price: $89.95    Price: $100.00

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 Shupp Cap
Sale Price: $49.95    Price: $55.00

The Bailey Shupp Cap- The Bailey Shupp Cap is a fine wool ascot cap blocked to shape and smoothly finished. The seamless style is accented with a small ventilated grommet on the side to allow som ... Read more »
Bailey Stingy Brim Hat
Sale Price: $172.50    Price: $213.00

The Bailey Stingy Fur Felt Fedora- The Bailey Stingy Fur Felt Fedora is a gorgeous 100% genuine fur felt fedora with a classic center dent crown and its namesake stingy 2 inch brim that can be wo ... Read more »
Bailey Montecristi Teardrop Crown Panama Hat
Sale Price: $575.00    Price: $625.00

The Bailey Montecristi Teardrop Crown Panama Hat is a beautiful classic look for summer- a fine quality tightly woven panama straw hat in a crisp white bleach color, shaped with a deep teardrop c ... Read more »