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 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 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 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 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 Wardell Lanolux Hat
Sale Price: $117.50    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 teardrop crown and 2 5/8 inc ... Read more »
Bailey Vito Flexible Braid Hat
Sale Price: $65.95    Price: $70.00

The Bailey Vito Flexible Braid Hat is a casual short brimmed fedora perfect for daily wear. The teardrop crown is a classic look, and the 1 5/8 inch stingy brim is a modern touch that can be worn ... Read more »
Bailey Verlin Bucket Hat
Sale Price: $51.95    Price: $60.00

The Bailey Verlin Bucket hat is a practical hat that remains stylish, made from a lightweight wool blend in a smooth olive melange that gives it a crisp modern look and a comfortable feel. The cl ... Read more »
Bailey Silko Diamond Crown Hat
Sale Price: $78.95    Price: $85.00

The Bailey Silko Diamond Crown Hat is a diamond crown fedora with exceptional style. The flattering shape is enhanced by a stingy 1 1/2 inch brim which can be snapped down or worn up all around. ... Read more »
Bailey Rollin Doeskin Hat
Sale Price: $127.50    Price: $135.00

The Bailey Rollin Doeskin Hat is a round crown traditional style with a wide 3 1/4 inch flat brim. A slim leather hat band gives it a unique look that can be dressed up or worn casually. Made fro ... Read more »
Bailey Obie Packable Wool Felt Hat
Sale Price: $99.95    Price: $105.00

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 Noble Superior Fur Felt Fedora Hat
Sale Price: $332.50    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 Mahlon Leather Bucket Hat
Sale Price: $139.95    Price: $150.00

The Bailey Mahlon Leather Bucket Hat is a hat made for travel and adventure. Buttery smooth leather only gets better with age, growing softer and ganing more character with every wear. The casual ... Read more »
Bailey Lemuel Superior Fur Felt Fedora Hat
Sale Price: $332.50    Price: $350.00

The Bailey Lemuel Superior Fur Felt Fedora Hat is a high quality traditional wide brimmed fedora with a center dent crown and generous 3 3/4 inch brim. The simple ribbon hat band keeps the look s ... Read more »
Bailey Ike Wool Felt Trilby Hat
Sale Price: $52.95    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: $84.95    Price: $90.00

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 Hiram Doeskin Hat
Sale Price: $118.00    Price: $125.00

The Bailey Hiram Doeskin Hat has a unique pushed out center dent crown for an easy, broken-in look with a slightly rounded shape. The wide 2 7/8 inch brim is wider without being overwhelming, and ... Read more »
Bailey Herbert Cashlux Hat
Sale Price: $129.95    Price: $143.00

The Bailey Herbert Cashlux Hat is a modern take on the traditional homburg hat, with a soft centerdent crown and a bound-edge roll brim. The shorter 1 1/2 inch brim keeps this hat looking new, an ... Read more »
Bailey Gaston Litefelt Hat
Sale Price: $89.95    Price: $95.00

The Bailey Gaston Litefelt Hat is a low profile fedora with a front pinch and 2 1/2 inch snap brim that curves up in the back and down in front for the classic fedora style. This handsome hat has ... Read more »
Bailey Ellsworth Litefelt Hat
Sale Price: $97.50    Price: $105.00

The Bailey Ellsworth Litefelt Hat is a striking centerdent fedora that updates a traditional style with modern technology. Made from water and wind resistent Litefelt, this hat is soft and flexib ... Read more »
Bailey Edsel Superior Fur Felt Fedora Hat
Sale Price: $299.95    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 Draper II Superior Fur Felt Fedora Hat
Sale Price: $307.50    Price: $325.00

The Bailey Draper II Superior Fur Felt Fedora is a remake of the popular Draper style fedora, with its lightly pinched front crown and flattering 2 1/4 inch snap brim. A slim ribbon hat band keep ... Read more »
Bailey Donal Wool Felt Fedora Hat
Sale Price: $64.95    Price: $70.00

The Bailey Donal Wool Felt Hat is a handsome traditional fedora with a few modern touches. The sharp center dent crown has a distinct front pinch and the hat has a flattering 2 1/4 inch brim that ... Read more »
Bailey Delbert Cashlux Hat
Sale Price: $129.95    Price: $138.00

The Bailey Delbert Cashlux Hat is a sharp looking centerdent crown fedora with a flattering 2 inch brim that can be snapped down in front. Made of fine Cashlux cashmere blended wool, this hat has ... Read more »
Bailey Cleve Roll Up Hat
Sale Price: $112.50    Price: $120.00

The Bailey Cleve Roll Up Hat is a brilliant design for the perfect travel accessory. The rounded pinch front crown has a distinctive, flattering look and the 2 inch relaxed brim is an attractive ... Read more »
Bailey Burl Superior Fur Felt Fedora Hat
Sale Price: $307.50    Price: $325.00

The Bailey Burl Superior Fur Felt Fedora is a classic center dent crown fedora with a flattering 2 inch snap brim and a sleek simple style trimmed with a traditional ribbon hat band. Made from lu ... Read more »
Bailey Bertram Litefelt Fedora Hat
Sale Price: $89.95    Price: $98.00

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 Benny Cashlux Hat
Sale Price: $139.95    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 Basil Litefelt Hat
Sale Price: $104.95    Price: $113.00

The Bailey Basil Litefelt Hat is a sharp looking hat for cool weather, with a center dent crown and short 1 3/4 inch brim that can be snapped down in front. Trimmed with a wide double bow hat ban ... Read more »
Bailey Arvid Wool Felt Porkpie Hat
Sale Price: $54.95    Price: $60.00

The Bailey Arvid Wool Felt Porkpie Hat is a classic look favored by musicians and brought back into popular fashion recently for its distinctive style. The wool felt flat telescope crown is exper ... Read more »
Bailey Artis Lanolux Hat
Sale Price: $118.50    Price: $125.00

The Bailey Artis Lanolux Hat is an attractive low profile pinch front fedora with a 2 1/2 inch downbrim and classic centerdent crown. This versatile hat has a striped ribbon hat band and is made ... Read more »
Bailey Arthur Cashlux Hat
Sale Price: $129.95    Price: $138.00

The Bailey Arthur Cashlux Hat is a touchably soft cashmere blend trilby with a pre-snapped stingy brim and a form-fitting rear slope crown for a less bulky look. A simple ribbon hat band keeps th ... Read more »
Bailey Dorsey Quilted Trapper Hat
Price: $213.00

The Bailey Dorsey Quilted Trapper Hat is designed to keep out the snow in style. Made from rich, soft leather, the outer shell is quilted for a padded feel and extra warmth in the coldest weather ... Read more »
Bailey Albin Quilted Trapper Hat
Sale Price: $106.95    Price: $113.00

The Bailey Albin Quilted Trapper Hat is an ideal companiion for the snowy days of winter. The classic trapper style has long earflaps which can be buckled at the crown when not in use and are lin ... Read more »
Bailey Writer Baseball Cap
Sale Price: $41.95    Price: $45.00

The Bailey Writer Baseball Cap is a simple, streamlined wool blend baseball cap in the traditional style. A paneled crown has a button top and small ventilating grommets on each panel. The front ... 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 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 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: $99.95    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 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 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 »