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Bailey of Hollywood Hats

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 evolved from fine dress headwear to include a Western and Outdoor collection, allowing Bailey to segue into a broader market. Bailey Hats are known for the craftsmanship of their product; quality that is apparent in all styles and luxury fibers and fabrics including fur felt, leather, genuine Panama, straw, wool and cloth hats and caps.

Classic styles such as fedoras, godfathers and derby’s were engineered and popularized by Bailey Hats in the 1920’s. Bailey Hats were seen on silver screen icons like Clark Gable and Humphrey Bogart. These individually handcrafted hats last a lifetime and always carry a strong and sophisticated look. The hats are durable and most provide protection in any weather.

Staying true to our history of fine craftsmanship and detailing, the Bailey brand continues to evolve in design with industry leading innovations in hat finishes and fine trim detailing. Our ranges feature classic and contemporary styling.

With the foundation of a long and proud heritage, world-renowned quality, innovation, and fashion forward styling, Bailey Hats continues to be a leader in the western, fashion and casual men’s hat arena.

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Bailey Galvin Wool - Wool Flat Cap Bailey Galvin Wool - Wool Flat Cap $58.48 ($64.98) 0-2 weeks
Bailey Kroft - Straw Fedora Hat Bailey Kroft - Straw Fedora Hat $55.78 ($61.98) 0-2 weeks
Bailey Myatt – Fedora Hat Bailey Myatt – Fedora Hat $60.28 ($66.98) 0-2 weeks
Bailey Morken - Straw Fedora Hat Bailey Morken - Straw Fedora Hat $72.23 ($84.98) 0-2 weeks
Bailey Wilshire - Straw Fedora Hat Bailey Wilshire - Straw Fedora Hat $53.98 ($59.98) 0-2 weeks
Bailey Port - Wool Flat Cap Bailey Port - Wool Flat Cap $47.68 ($52.98) 0-2 weeks
Bailey Basil - Soft Wool Fedora Hat Bailey Basil - Soft Wool Fedora Hat $83.28 ($97.98) 0-2 weeks
Bailey Mannes - Straw Fedora Hat Bailey Mannes - Straw Fedora Hat $48.58 ($53.98) 0-2 weeks
Bailey Hinton - Flat Cap - Closeout Bailey Hinton - Flat Cap - Closeout $21.99 ($43.98) 0-2 weeks
Bailey Greyson - Straw Fedora Hat Bailey Greyson - Straw Fedora Hat $52.18 ($57.98) 0-2 weeks
Bailey Bellamy - Wool Aviator Cap Bailey Bellamy - Wool Aviator Cap $64.58 ($75.98) 0-2 weeks
Bailey Suntino - Straw Fedora Hat Bailey Suntino - Straw Fedora Hat $55.78 ($61.98) 0-2 weeks
Bailey Loche - Straw Fedora Hat Bailey Loche - Straw Fedora Hat $83.28 ($97.98) 0-2 weeks
Bailey Arch - Straw Fedora Hat Bailey Arch - Straw Fedora Hat $59.38 ($65.98) 0-2 weeks
Bailey Graham - Cloth Flat Cap Bailey Graham - Cloth Flat Cap $37.78 ($41.98) 0-2 weeks
Bailey Waits - Straw Porkpie Hat Bailey Waits - Straw Porkpie Hat $54.88 ($60.98) 0-2 weeks
Bailey Egan - Flat Cap Bailey Egan - Flat Cap $52.18 ($57.98) 0-2 weeks
Bailey Artis - Wool Fedora Hat Bailey Artis - Wool Fedora Hat $97.73 ($114.98) 0-2 weeks
Bailey Harston - Cloth Flat Cap Bailey Harston - Cloth Flat Cap $39.58 ($43.98) 0-2 weeks
Bailey Hayward - Straw Porkpie Hat Bailey Hayward - Straw Porkpie Hat $100.78 ($125.98) 0-2 weeks
Bailey Spivy - Wool Porkpie Hat Bailey Spivy - Wool Porkpie Hat $63.88 ($70.98) 0-2 weeks
Bailey Mollien - Soft Wool Fedora Hat Bailey Mollien - Soft Wool Fedora Hat $50.38 ($55.98) 0-2 weeks
Bailey Paley - Straw Fedora Hat Bailey Paley - Straw Fedora Hat $100.78 ($125.98) 0-2 weeks
Bailey Bendrix - Straw Fedora Hat Bailey Bendrix - Straw Fedora Hat $59.38 ($65.98) 0-2 weeks
Bailey Jimson - Straw Fedora Hat Bailey Jimson - Straw Fedora Hat $97.73 ($114.98) 0-2 weeks
Bailey Draper II - Fur Fedora Hat Bailey Draper II - Fur Fedora Hat $219.98 ($274.98) 0-2 weeks
Bailey Cavell - Soft Wool Felt Fedora Hat Bailey Cavell - Soft Wool Felt Fedora Hat $93.48 ($109.98) 0-2 weeks
Bailey Riff - Soft Wool Felt Fedora Hat Bailey Riff - Soft Wool Felt Fedora Hat $84.13 ($98.98) 0-2 weeks
Bailey Harker - Wool Derby Hat Bailey Harker - Wool Derby Hat $73.08 ($85.98) 0-2 weeks
Bailey Baxter - Cloth Fedora Hat Bailey Baxter - Cloth Fedora Hat $59.38 ($65.98) 0-2 weeks

Displaying 0-20 of 161 results Sort by: View: