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 September 21, 2015

100 Top Transitional Picks

A smart selection of wardrobe staples for the season ahead

Sale Ended September 05, 2015

Ivy League-Inspired Tailoring

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

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 27, 2015

Fall Essentials: Military Outerwear

This season’s best outerwear takes its design orders from classic military silhouettes

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