In the post-Bogart age, the fedora is a double-or-nothing wager that will land you in the losers’ circle far more often than it will pay out. But for guys who can back up the bet, the returns can be handsome. You’ve seen Brad and Johnny carry it off. Perhaps you’ve watched Mad Men’s Don Draper toss his felt aside after walking into a room like he owns it and thought to yourself, I could make that work. Maybe you went so far as to buy one. But beware the hat trap. Before you venture out—to a place where a chapeau isn’t required by a costume theme or as a prop to distract paparazzi—consider how that fabric atop your head will define you.

“You have to feel like you own that piece,” says Kevin Harter, men’s fashion director at Bloomingdale’s. But confidence can take you only so far; a false tip, a clumsy doff, or an incorrect fit can render your cap dunced. If you’re in your twenties, there’s a chance you can get away with the casual fedora, as long as you keep what’s south of your chin simple. Avoid necklaces, graphic T-shirts, and vests, which, when paired with a hat, may cause a chemical reaction that results in Pete Wentz. If you’re in your late thirties or early forties, a classic gray fedora can be a smart and practical partner for a suit, provided you stay away from ridiculous embellishments. Shape, size, and positioning make all the difference: A fedora shouldn’t be perched high on your crown or squashed down on your brow. It should frame your eyes but not hide your face. “Stick with smaller brims,” says Banana Republic creative director Simon Kneen, “or you run the risk of looking like Oscar Wilde.” And while a gentle tilt is acceptable, cocking at an extreme angle is strictly for Dick Tracy.

Still think you have what it takes? Go for it. If not, try flipping the hat over and asking for change.

Written by Courtney Colavita. Article used with permission.

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