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Bailey Spring/Summer Hats

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.

Bailey's new season of warm weather hats are perfect for any occasion or adventure. With classics like the Bailey Billy Packable hat or if you're looking for something new and modern check out the Bailey Inman Litestraw Porkpie Hat.

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 Chaplin Bowler Hat
Sale Price: $127.50    Price: $150.00

The Bailey Chaplin Bowler Hat is a brilliant warm weather version of the classic round crown derby. Made of lightweight panama straw with a flexible 2 inch bound edge brim, this hat features a wi ... Read more »
Bailey Thurman Panama Hat
Sale Price: $127.50    Price: $150.00

The Bailey Thurman Panama Hat is a classic style centerdent panama straw fedora with a tight flexible weave and a handsome silhouette. A 2 1/4 inch pre-snapped brim shades the eyes while the sim ... Read more »
Bailey Hanson Shantung Hat
Sale Price: $93.50    Price: $110.00

The Bailey Hanson Shantung Hat is a light Shantung fedora with a center dent crown and 2 1/2 inch snap brim. A crisp classic look, this hat is finished with a slim black ribbon hat band and a rem ... Read more »
Bailey Guthrie Litestraw Hat
Sale Price: $93.50    Price: $110.00

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 comfortable int ... Read more »
Bailey Loring Genuine Panama Fedora
Sale Price: $233.75    Price: $275.00

The Bailey Loring Genuine Panama Fedora is a beautifully made 100% genuine Grade 8 panama straw hat hand woven in Ecuador and finished in the USA. The modern grad crown has a slight slope in both ... Read more »
Bailey Milo Panama Hat
Sale Price: $127.50    Price: $150.00

The Bailey Milo Panama Hat is a bold new look for the classic panama fedora. Made from handwoven 100% toquilla palm, this two-tone hat has a zig zagged chevron pattern and a flattering 2 1/2 inch ... Read more »
Bailey Sydney Panama Hat
Sale Price: $127.50    Price: $150.00

Bailey Sydney is a Genuine Panama Hat hand-woven in Ecuador and finished in the USA. Sydney; included in the Bailey Casual Straw hat Collection comes in several colors. The hat has a teardrop c ... Read more »
Bailey Blackburn Litestraw Fedora
Sale Price: $102.00    Price: $120.00

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 Lando Hat
Sale Price: $63.75    Price: $75.00

The Bailey Lando Hat is a classy summer fedora, woven from smooth flexible paper straw for a soft feel. Comfortable and classic, the centerdent crown and medium width pre-snapped brim are looks t ... 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 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 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 Salem Packable Hat
Sale Price: $51.00    Price: $60.00

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 Archer Braid Fedora
Sale Price: $57.80    Price: $68.00

The Bailey Archer Braid Fedora is a short brimmed trilby fedora with a teardrop crown and stingy 1 5/8" snap brim for a modern silhouette. There is a two-tone stripe around the top of the crown t ... Read more »
Bailey Mannesroe Hat
Sale Price: $51.00    Price: $60.00

The Bailey Mannesroe Hat is a flexible braid fedora with a classic center dent crown and 2 inch snap brim. This handsome hat is multi-colored, with a solid crown and multi-braid brim. The hat ban ... Read more »
Bailey Waits Braid Porkpie Hat
Sale Price: $59.50    Price: $70.00

The Bailey Waits Braid Porkpie Hat is a fashionable packable hat with a telescope crown and short 1 5/8" brim that can be worn turned up or snapped down in front. A sharp looking hat, the wide ri ... Read more »
Bailey Grimet Braided Fedora Hat
Sale Price: $59.50    Price: $70.00

The Bailey Grimet Braided Fedora Hat is an exceptionally soft braided fedora with a fashionable 1 3/4 inch brim that can be snapped down in front or worn up all around. Flexible, packable and lig ... Read more »
Bailey Kroft Hat
Sale Price: $59.50    Price: $70.00

The Bailey Kroft Hat is a fashionable trilby-style fedora with a teardrop crown and a fashionable 1 5/8" snap brim. Made from flexible braid and finished with a self hat band, this packable ... Read more »
Bailey Wilshire Hat
Sale Price: $59.50    Price: $70.00

The Bailey Wilshire Hat is a crushable, comfortable fedora ideal for warm weather. A rounded teardrop crown gives it a softer shape, while the 2 inch brim cap be snapped down in front for style a ... Read more »
Bailey Billy Packable Hat
Sale Price: $51.00    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 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 Mannes Hat
Sale Price: $51.00    Price: $60.00

Bailey Mannes is a multi-colored braid 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 a narr ... Read more »
Bailey Pirkis Cap
Sale Price: $53.10    Price: $62.50

The Bailey Pirkis Cap is a crisp summer cap in the classic ivy style, with a smooth crown and short front peak. Ideal for golf or just a stroll around town, this cheerful cap has a windowpane pla ... Read more »
Bailey Dormer Cap
Sale Price: $68.00    Price: $80.00

The Bailey Dormer Cap is a simple, classic ivy style cap. Made from lightweight summer fabric, this cap is a great timeless look that goes with everything, taking it from dressed up to dressed do ... Read more »
Bailey Slater Cap
Sale Price: $44.20    Price: $52.00

The Bailey Slater Cap is a handsome ivy style flat cap with a smooth crown and paneling in the back for texture and a close, sleek fit. Made of lightweight summer weight suiting fabric and lined ... Read more »
Bailey Jackman Hat
Sale Price: $89.25    Price: $105.00

The Bailey Jackman Hat is a perfect hat for travel. Made of lightweight soft wool, this fedora crown hat has a 2 1/2 inch casual brim and thin hat band. The hat is packable, crushable, and comes ... Read more »
Bailey Ashmore Hat
Sale Price: $89.25    Price: $105.00

The Bailey Ashmore Hat is a part of the Bailey Poet Travel Collection; a packable, foldable hat made for bringing along, this soft rustic Litefelt hat is water and weather resistant with a slight ... 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 Brooks Panama Hat
Sale Price: $119.00    Price: $140.00

Bailey Brooks is a Genuine Panama Hat with a teardrop crown and a 2 3/8 inch downbrim. Brooks has a grosgrain hat band and an interior sweatband. This hat has a heavier body. Hand-woven in Ecuado ... Read more »
Bailey Cutler Panama Hat
Sale Price: $119.00    Price: $140.00

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 comfo ... Read more »
Bailey Joad Litestraw Hat
Sale Price: $89.25    Price: $105.00

The Bailey Joad Litestraw Hat is an outdoorsy hat with a lot of style. The teardrop crown slopes down into a 2 1/2" turned down brim to shade the eyes and give the hat a more casual, easy feel. T ... Read more »
Bailey Spencer Litestraw Hat
Sale Price: $63.75    Price: $75.00

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 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 Elliott Trilby Hat
Sale Price: $51.00    Price: $60.00

The Bailey Elliott is a straw braid trilby style fedora with a pinched front crown and snapped down 2" brim. This contemporary looking straw hat has a simple fabric hat band and is a light b ... Read more »
Bailey Foley Braided Straw Fedora
Sale Price: $63.75    Price: $75.00

The Bailey Foley Braided Straw Fedora combines the delicate look of finely woven straw with the durable, flexible feel of Litestraw for a hat made for summer. A casual grad crown, slightly sloped ... Read more »
Bailey Harston Ivy Style Cap
Sale Price: $46.75    Price: $55.00

The Bailey Harston Ivy Style Cap is a sleek classic style ivy cap with a smooth crown and sleek lines. Made from light, crisp summer linen, this cap is ideal for staying stylish on the hottest su ... Read more »
Bailey Redford Newsboy Cap
Sale Price: $46.75    Price: $55.00

The Bailey Redford Newsboy Cap is a handsome dockman cap with a slightly rounded shape and paneled crown. This classic look is always fashionable, and here in cotton pickstitch pinstripe it is a ... Read more »
Bailey Graham Cap
Sale Price: $38.25    Price: $45.00

The Bailey Graham is an all-weather cap made from 65% polyester and 35% cotton fabric. This cap features a unique five-piece design, angular side seam, and interior lining. Made in China. ... Read more »
Bailey Dalton Rain Safari Hat
Sale Price: $46.75    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 Konrath Hat
Sale Price: $127.50    Price: $150.00

The Bailey Konrath Hat is a lightstraw fedora made from a premium shantung which makes this hat durable, flexible, and gives it water resistance. A classic style fedora with a teardrop crown and ... Read more »
Bailey Crampton Endura Straw Fedora
Sale Price: $89.25    Price: $105.00

Endura Finish hats have a revolutionary, thermosetting yarn inserted inside paper straw fiber prior to being woven. The result is a shape retentive hat that will return to it's blocked shape even ... Read more »
Bailey Barrett Endura Straw Fedora
Sale Price: $85.00    Price: $100.00

Endura Finish hats have a revolutionary, thermosetting yarn inserted inside paper straw fiber prior to being woven. The result is a shape retentive hat that will return to it's blocked shape even ... Read more »
Bailey Engman LiteStraw Fedora
Sale Price: $85.00    Price: $100.00

The Bailey of Hollywood Engman LiteStraw® is made with Toyo LiteStraw® that is supple, shape retentive, and water repellent. This stylish spring and summer fedora has a 2 7/8" brim, a grad crown, ... Read more »
Bailey Harvey Shantung Fedora
Sale Price: $119.00    Price: $140.00

This Bailey of Hollywood spring and summer hat is a western shantung straw style. The Harvey Fedora includes details like a pinch front crown, a 3 1/2"" flat brim, and a Dri-Lex® sweatband. Finis ... Read more »
Bailey Bayard LiteStraw Fedora
Sale Price: $80.75    Price: $95.00

The Bailey of Hollywood Bayard LiteStraw® is made with Toyo LiteStraw® that is supple, shape retentive, and water repellent. This stylish spring and summer fedora has a 2 3/8" casual brim, a tear ... Read more »
Bailey Torslef Straw Fedora
Sale Price: $63.75    Price: $75.00

The Bailey of Hollywood Torslef Fedora, part of the Poet collection, is a Toyo crochet straw hat style for spring and summer. The Torslef features a 2 3/4" brim, a comfort sweatband, and a jute s ... Read more »
Bailey Pelly Braided Trilby
Sale Price: $59.50    Price: $70.00

Cool braided styles are an excellent shape for the spring and summer seasons! The Bailey of Hollywood Pelly Braided Trilby has a stingy 1 5/8" snap brim, a comfort sweatband, and a teardrop crown ... Read more »
Bailey Frankie Straw Fedora
Price: $59.50

A cool, relaxed spring and summer style, the Bailey of Hollywood Frankie Fedora features a stingy 1 5/8" snap brim, a center dent crown, and a comfort sweatband. The Frankie is made with a melang ... Read more »
Bailey Garrell Braided Fedora
Sale Price: $63.75    Price: $75.00

A fantastic summer style that fits right in at the beach, resort, or deck party! The Bailey of Hollywood Garrell Braided Fedora is a melange dye braid style with a vented crown and a straw hatban ... Read more »