Waits Braided Pork Pie

$44

Pork pies became a fashion favorite due to 1920s American actor Buster Keaton. Converting fedoras into pork pie hats for his films, Keaton made them an iconic fashion choice for any man. Discover your own love for pork pies when you shop the Bailey’s Waits Pork Pie Hat at Hats.com. Nearly as popular today as they were in the 1920s, this particular hat offers a sleek, smooth braided style with a grosgrain ribbon band and classic telescoping crown. The brim is rather small — offering a 1 ⅝” stingy turned-up brim.

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Lightning 4X Cowboy Western Hat

$110

You might not know a saddle from a spur, but you don't need to spend a lot of time on the trail to appreciate the comfort and craftsmanship of this silver-buckled hat from the reliably stylish Bailey collection. Made from a fur-wool felt blend and available in an abundance of colors, it's guaranteed to upend your expectations of a traditional men's Western hat.

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Wickes Flat Cap

$77

The Wickes Flat cap by Bailey 1922 is a new 5 point cap with convertible ear-flaps. Made from a wool-blend and fully lined, the Wickes is a great option for cold-weather days. it is finished with a comfort sweatband.

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