Porkpie

Similar to a fedora, but without the peaked crown and pinched front. Perfect if you want to look like a jazz man from the ’50s. …
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Beret

Slip one of these babies on your head, and you can’t help it — you just feel French. (Attitude not included.) …
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Ball Cap

Every dude’s fallback headwear. Caps look best with casual clothes, and if you’re considering the sideways look, leave it to young guys. …
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Trilby

Often confused with a fedora, this pinched-front hat has a narrow brim, perfect for those of us with narrower shoulders. …
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Fez

No matter how dignified you think you may look with a fez, it’s a tricky look to pull off. Best with a smoking jacket or in a James Bond movie. …
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Fedora

Ah, that classic Humphrey Bogart/Indiana Jones look. Broad-brimmed fedoras are best for those with broad shoulders. Alas, not me. …
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