Bailey Hats by NewUrban Hats. Here you will find the key styles of Bailey trilby hats, Bailey fedora hats, Bailey pork pie hats for both summer and winter and also the latest Bailey flat caps.

Key styles include the Bailey Wynn Trilby hat, the Bailey Darron Pork Pie hat and the Bailey Tino Felt Trilby hat.

The Bailey Hat Company was founded in 1922 by George S. Bailey in Los Angeles, California and it wasn't long before he was fashioning Hollywood A-Listers Humphrey Bogart, Cary Grant, Bing Crosby and Gary Cooper, cementing his place as Hollywood's premiere milliner. Most Bailey hats are still made in the USA today, with styling that is quintessential America.

You can refine your search by using our selection tools below where you can search by hat brand, hat style, weather type, size and colour
Set Descending Direction
Bailey Wynn Felt Crushable Trilby Hat – Black

Bailey

Bailey Wynn Felt Crushable Trilby Hat – Black

£32.00
Bailey Tino Crushable Fedora Hat - Black

Bailey

Bailey Tino Crushable Fedora Hat - Black

£35.00
Bailey Klassen Cap - Vivid Blue Plaid

Bailey

Bailey Klassen Cap - Vivid Blue Plaid

£24.95
Bailey Tesser Cap – Grey Mix Plaid

Bailey

Bailey Tesser Cap – Grey Mix Plaid

£24.95
Bailey Taft Cap – Atlantic Blue Plaid

Bailey

Bailey Taft Cap – Atlantic Blue Plaid

£24.95
Bailey Pendergrass Cap – Bale Olive

Bailey

Bailey Pendergrass Cap – Bale Olive

£24.95
Bailey Pendergrass Cap – Bale Light Grey

Bailey

Bailey Pendergrass Cap – Bale Light Grey

£24.95
Bailey Elias Cap – Atlantic Blue

Bailey

Bailey Elias Cap – Atlantic Blue

£27.75
Bailey Elias Cap – Natural

Bailey

Bailey Elias Cap – Natural

£27.75
Bailey Mannes Straw Trilby - Navy

Bailey

Bailey Mannes Straw Trilby - Navy

£28.95
Bailey Mannes Straw Trilby – Charcoal

Bailey

Bailey Mannes Straw Trilby – Charcoal

£28.95
Bailey Mannes Straw Trilby – Grain

Bailey

Bailey Mannes Straw Trilby – Grain

£28.95
Bailey Billy Straw Trilby – Lake

Bailey

Bailey Billy Straw Trilby – Lake

£28.95
Bailey Billy Straw Trilby – White

Bailey

Bailey Billy Straw Trilby – White

£28.95
Bailey Billy Straw Trilby – Black

Bailey

Bailey Billy Straw Trilby – Black

£28.95
Bailey Charlie Straw Pork Pie Hat – Stallion

Bailey

Bailey Charlie Straw Pork Pie Hat – Stallion

£28.95
Bailey Charlie Straw Pork Pie Hat – Black

Bailey

Bailey Charlie Straw Pork Pie Hat – Black

£28.95
Bailey Tennessee Straw Trilby – Tan Brown

Bailey

Bailey Tennessee Straw Trilby – Tan Brown

£28.95
Bailey Tennessee Straw Trilby – Tan Blue

Bailey

Bailey Tennessee Straw Trilby – Tan Blue

£28.95
Bailey Maynard LiteStraw Trilby – Dark Grey

Bailey

Bailey Maynard LiteStraw Trilby – Dark Grey

£49.95
Bailey Sawyer Panama Fedora – Brown

Bailey

Bailey Sawyer Panama Fedora – Brown

£99.95
Bailey Guthrie LiteStraw Trilby – Natural

Bailey

Bailey Guthrie LiteStraw Trilby – Natural

£49.95
Bailey Carnegie Panama Fedora Hat – Natural

Bailey

Bailey Carnegie Panama Fedora Hat – Natural

£75.00
Bailey Mayron Newsboy Cap – Grey Plaid

Bailey

Bailey Mayron Newsboy Cap – Grey Plaid

£24.95
Bailey Wynn Felt Crushable Trilby Hat – Grey

Bailey

Bailey Wynn Felt Crushable Trilby Hat – Grey

£32.00
Bailey Brandt Lanolux Felt Fedora Hat

Bailey

Bailey Brandt Lanolux Felt Fedora Hat

£59.99
Bailey Augustin Fur Felt Trilby Hat – Hemlock

Bailey

Bailey Augustin Fur Felt Trilby Hat – Hemlock

£99.99
Bailey Augustin Fur Felt Trilby Hat – Black

Bailey

Bailey Augustin Fur Felt Trilby Hat – Black

£99.99
Set Descending Direction