Bailey of Hollywood & more

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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

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Past Sales Featuring Bailey of Hollywood & more

Sale Ended November 14, 2015

Black on Black

Head-to-toe looks to capture the effortless, cool kid vibe

Sale Ended September 05, 2015

Ivy League-Inspired Tailoring

Back-to-campus classics, featuring Smart Turnout's clever closet staples and accessories

Sale Ended August 31, 2015

Fall Stock-Up: Boots

The newest batch of seasonal essentials are here, from cozy cashmere to built-to-last boots

Sale Ended November 02, 2015

Fall’s Best Sportcoats: Up to 70% Off

Dress up your favorite jeans with these standout jackets

More Styles by Bailey of Hollywood