What: The fedora. Frank Sinatra wore it. Gregory Peck. Keith Richards. And it’s as cool now as it was then – think Johnny Depp, Justin Timberlake, Usher. They’re cool, right?

Don’t just take my word for it: From Amanda Brooks at Men’s Vogue: “. . . fedoras are also the ultimate test of individuality. You just can’t pull off wearing one unless you are unusually confident, daring, and nonchalant. All that said, men who sport hats of any kind can get away with just about anything as far as I’m concerned.”

Buy It: For the fully style-confident among you, try this plaid number from Target, for an easy $14.99. For a more classic take, try the same style in a basic black pinstripe.

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