Bailey of Hollywood & more

Looks still available

See All Bailey of Hollywood Products

About Bailey of Hollywood

If you’ve ever watched a classic black-and-white movie and found yourself coveting the suave leading man’s hat, there’s a strong chance you were admiring the work of Bailey of Hollywood. Founded in 1922 by Los Angeles-based entrepreneur George S. Bailey, Bailey of Hollywood spent the Golden Age of cinema designing headwear for some of Hollywood’s biggest legends — Cary Grant, Humphrey Bogart, and Gary Cooper, just to name a few. Bailey of Hollywood continues to produce classic fedora, Trilby and pork pie hats as well as authentic Western-style cowboy hats and baseball caps. Whether you’re going for an old-time gangster look or striving to out-cool the Marlboro Man, you’ll find exactly what you’re looking for in Bailey of Hollywood’s well-constructed collections.

New Sales Featuring Bailey of Hollywood & more

Shop 2 New Sales

Past Sales Featuring Bailey of Hollywood & more

Sale Ended September 21, 2015

100 Top Transitional Picks

A smart selection of wardrobe staples for the season ahead

Sale Ended September 02, 2015

Buyer's Pick: Monkstraps

Classic iterations of the most elegant shoe out there by Bruno Magli, Cole Haan, and more

Sale Ended September 24, 2015

Black Dress Shoes

Wingtips, monkstraps, and more refined footwear for every occasion by top quality brands including Wall + Water

Sale Ended September 08, 2015

Dress Shoes: Up to 80% Off

Can't-miss deals on refined footwear from our favorite brands, including Antonio Maurizi and testoni BASIC

More Styles by Bailey of Hollywood