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Bailey Hats

Bailey Hats come with with the authority of world-renowned quality and a deep and proud heritage, fashion forward styling with innovation in hat technology. The Bailey Hat continues to be a leader in the mens hats, fedora, straw, fashion hat arena. Bailey of Hollywood Hats ® was founded in 1922 by George Bailey as a fine dress headwear artisan, priding itself on the brands philosophy on professionally crafted hats. Bailey Hats matured from fine dress headwear to incorporate western style and outdoor ranges, allowing Bailey of Hollywood to diversify into a broader market.

Bailey Hats are renowned for the quality and the craftsmanship of their product that is prevalent throughout the range. Constructed using luxury fabrics and fibres including genuine Panama, fur felt, leather caps. Classic styles such as the derby’s, fedoras and godfathers were introduced and then popularised in the 1920'. Bailey of Hollywood Hats were seen endorsed screen icons from Humphrey Bogart to Clark Gable. When you buy Bailey hats online your are buying into the Bailey philosophy of individually hand crafted hats that will last a life time, and carrying a strong and sophisticated look with it proved to be a hit.

Staying true to their history of detailing and fine craftsmanship, the Bailey marque continues to develop with industry leading innovations and design, fine trim detailing and hat finishes. This season there are some absolute gems to choose from, our editors picks are the Bailey Mannes straw hat - check out the new royal blue colour option for this season.  Also, new is the Bailey Lucas short brim straw hat, the Bailey Flat Caps; Jack and Graham not to mention the grandiose Bailey Lamar boater hat.  If your looking to make a statement then the Bailey Sheldon straw antique trilby is completely unique or the Crosby teardrop straw hat is another great option.


93 Products Found
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Bailey Laden Newsboy Cap - Blue Smoke Bailey Laden Newsboy Cap - Blue Smoke
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Laden Newsboy Cap - Blue Smoke

On Sale £28.00 Regular price
£40.00

-0%
Bailey Tino Felt Tribly Hat - Medium Brown Bailey Tino Felt Tribly Hat - Medium Brown
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Tino Felt Tribly Hat - Medium Brown

£59.00

-0%
Bailey Riff Felt Tribly Hat - Cognac Brown Bailey Riff Felt Tribly Hat - Cognac Brown
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Riff Felt Tribly Hat - Cognac Brown

£69.00

-0%
Bailey Blixen Widebrim Fedora Hat - Black Bailey Blixen Widebrim Fedora Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Blixen Widebrim Fedora Hat - Black

£60.00

-0%
Bailey Jackman Unstructured Fedora Hat - Black Bailey Jackman Unstructured Fedora Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Jackman Unstructured Fedora Hat - Black

£65.00

-0%
Bailey Chipman Unstructured Tribly Hat - Silver Belly Bailey Chipman Unstructured Tribly Hat - Silver Belly
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Chipman Unstructured Tribly Hat - Silver Belly

£50.00

-0%
Bailey Galvin Wool Newsboy Cap - Camel Bailey Galvin Wool Newsboy Cap - Camel
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Galvin Wool Newsboy Cap - Camel

£44.00

-0%
Bailey Inglis Widebrim Fedora Hat - Silver Belly
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Inglis Widebrim Fedora Hat - Silver Belly

£60.00

-0%
Bailey Arvid Pork Pie Hat - Black Bailey Cole Cashmere Flat Cap - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Arvid Pork Pie Hat - Black

£45.00

-0%
Bailey Cole Cashmere Flat Cap - Black Bailey Cole Cashmere Flat Cap - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Cole Cashmere Flat Cap - Black

£50.00

-0%
Bailey Chipman Fedora Hat - Black Bailey Chipman Fedora Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Chipman Fedora Hat - Black

£55.00

-0%
Bailey Waits Pork Pie Hat - Smoke Bailey Waits Pork Pie Hat - Smoke
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Waits Pork Pie Hat - Smoke

£47.00

-0%
Bailey Inglis Widebrim Fedora Hat - Black Bailey Inglis Widebrim Fedora Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Inglis Widebrim Fedora Hat - Black

£55.00

-0%
Bailey Crowe Pork Pie Hat - Black Bailey Crowe Pork Pie Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Crowe Pork Pie Hat - Black

£55.00

-0%
Bailey Cloyd Trilby Hat - Navy Blue Bailey Cloyd Trilby Hat - Navy Blue
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Cloyd Trilby Hat - Navy Blue

£45.00

-0%
Bailey Timson Centre Crease Tribly Hat - Black Bailey Timson Centre Crease Tribly Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Timson Centre Crease Tribly Hat - Black

£50.00

-0%
Bailey Tino Felt Tribly Hat - Woodland Mix Bailey Tino Felt Tribly Hat - Woodland Mix
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Tino Felt Tribly Hat - Woodland Mix

£59.00

-0%
Bailey Vernon Trapper Hat - Brown Bailey Vernon Trapper Hat - Brown
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Vernon Trapper Hat - Brown

£129.00

-0%
Bailey Curtis Widebrim Fedora Hat - Oxford Grey Mix Bailey Curtis Widebrim Fedora Hat - Oxford Grey Mix
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Curtis Widebrim Fedora Hat - Oxford Grey Mix

£59.00

-0%
Bailey Curtis Widebrim Fedora Hat - Navy Blue Bailey Curtis Widebrim Fedora Hat - Navy Blue
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Curtis Widebrim Fedora Hat - Navy Blue

£59.00

-30%
Bailey Billy Light Trilby Hat - Dark Chino Bailey Billy Light Trilby Hat - Dark Chino
  • S
  • M
  • L
  • XL

Bailey Billy Light Trilby Hat - Dark Chino

On Sale £31.50 Regular price
£45.00

-0%
Bailey Wicket Straw Triby Hat - Black Bailey Wicket Straw Triby Hat - Black
  • Small (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • X-Large (60-61cm)

Bailey Wicket Straw Triby Hat - Black

£55.00

-0%
Bailey Wicket Straw Triby Hat - Cumin Bailey Wicket Straw Triby Hat - Cumin
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm

Bailey Wicket Straw Triby Hat - Cumin

£55.00

-30%
Bailey Spencer Straw Fedora Hat - Mineral Grey Bailey Spencer Straw Fedora Hat - Mineral Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Spencer Straw Fedora Hat - Mineral Grey

On Sale £38.50 Regular price
£55.00

-0%
Bailey Spencer Straw Fedora Hat - Natural Bailey Spencer Straw Fedora Hat - Natural
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Spencer Straw Fedora Hat - Natural

£55.00

-33%
Bailey Lando Straw Triby Hat - Natural Bailey Lando Straw Triby Hat - Natural
  • S (54-55cm)
  • MS (56-57cm)
  • LS (58-59cm)
  • XLS (60-61cm)

Bailey Lando Straw Triby Hat - Natural

On Sale £40.00 Regular price
£60.00

-33%
Bailey Lando Straw Triby Hat - Overcast Grey Bailey Lando Straw Triby Hat - Overcast Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Lando Straw Triby Hat - Overcast Grey

On Sale £40.00 Regular price
£60.00

-0%
Bailey Waits Pork Pie Hat - Steel Grey Bailey Waits Pork Pie Hat - Steel Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • X-Large (60-61cm)

Bailey Waits Pork Pie Hat - Steel Grey

£47.00

-0%
Bailey Waits Pork Pie Hat - Black Bailey Waits Pork Pie Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • Large (58-59cm)
  • XL (60-61cm)

Bailey Waits Pork Pie Hat - Black

£47.00

-20%
Bailey Archer Trilby Hat - Coffee Bailey Archer Trilby Hat - Coffee
  • S
  • M
  • L
  • XL

Bailey Archer Trilby Hat - Coffee

On Sale £36.00 Regular price
£45.00

-0%
Bailey Ellsworth Fedora - Black Bailey Ellsworth Fedora - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL(60-61cm)

Bailey Ellsworth Fedora - Black

£55.00

-0%
Bailey Cloyd Trilby Hat - Oxblood Bailey Cloyd Trilby Hat - Oxblood
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Cloyd Trilby Hat - Oxblood

£45.00

-0%
Bailey Antone Mountain Hat - Black Bailey Antone Mountain Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL(60-61cm)

Bailey Antone Mountain Hat - Black

£179.00

-0%
Bailey Darron Pork Pie Hat - Tobacco Bailey Darron Pork Pie Hat - Tobacco
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Darron Pork Pie Hat - Tobacco

£59.00

-50%
Bailey Donal Fedora Hat - Black Mix Bailey Donal Fedora Hat - Black Mix
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Donal Fedora Hat - Black Mix

On Sale £25.00 Regular price
£50.00

-0%
Bailey Cloyd Trilby Hat - Grey Bailey Cloyd Trilby Hat - Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Cloyd Trilby Hat - Grey

£45.00

-0%
Bailey Curtis Widebrim Fedora Hat - Grey Bailey Curtis Widebrim Fedora Hat - Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Curtis Widebrim Fedora Hat - Grey

£59.00

-0%
Bailey Dean Unstructured Fedora - Charcoal Grey Bailey Dean Unstructured Fedora - Charcoal Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL(60-61cm)

Bailey Dean Unstructured Fedora - Charcoal Grey

£60.00

-0%
Bailey Tino Trilby Hat - Bruise Mix Bailey Tino Trilby Hat - Bruise Mix
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Tino Trilby Hat - Bruise Mix

£59.00

-0%
Bailey Galvin Herringbone Newsboy Cap - Brown/Black Bailey Galvin Herringbone Newsboy Cap - Brown/Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Galvin Herringbone Newsboy Cap - Brown/Black

£44.00

-0%
Bailey Galvin Herringbone Newsboy Cap - Black/Grey Bailey Galvin Herringbone Newsboy Cap - Black/Grey
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Galvin Herringbone Newsboy Cap - Black/Grey

£44.00

-0%
Bailey Lord Herringbone Flat Cap - Brown/Black Bailey Lord Herringbone Flat Cap - Brown/Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Lord Herringbone Flat Cap - Brown/Black

£44.00

-60%
Bailey Verlin Bucket Hat - Olive Bailey Verlin Bucket Hat - Olive
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Verlin Bucket Hat - Olive

On Sale £18.00 Regular price
£45.00

-0%
Bailey Cloyd Trilby Hat - Black Bailey Cloyd Trilby Hat - Black
  • S (54-55cm)
  • M (56-57cm)
  • L (58-59cm)
  • XL (60-61cm)

Bailey Cloyd Trilby Hat - Black

£45.00

-46%
Bailey Nathaniel Beanie Hat - Navy Bailey Nathaniel Beanie Hat - Navy
  • One Size

Bailey Nathaniel Beanie Hat - Navy

On Sale £13.00 Regular price
£24.00