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.

Many of the styles by Bailey feature classic fedora and derby blocks. These hats often have a little touch of contemporary style to them, whether it be with a flared feather inside of the hat band, a laser-cut or tie style band, or a pattern along the crown that really sets off the hat's style. These classic styles (also found within the different Hats in the Belfry collections) are perfect for formal events, casual days, and even less dressier occasions that require that perfect touch to that great outfit.