There is the old reliable knit stocking cap. It looked good on you when you were 10 years old, and it still looks good -- on 10-year-olds. If you wear it as an adult, people will assume you just got back from a lengthy ice-fishing trip in northern Minnesota. There is the baseball cap. Nothing can beat it for conveying maturity and professionalism except maybe flip-flops and a Hawaiian shirt.
There is the fur hat once favored by members of the Soviet Politburo as they reviewed parades of missiles in Red Square. It once had a certain cachet, suggesting you were a formidable person with the means to invade Hungary if provoked. But when the Berlin Wall fell, this headgear became as obsolete as Lenin's corpse.
There is the beret. It's fine if you're French, or if you're taking a painting class at the local Art Institute. Otherwise, you might as well wear a sign around your neck with the words, "Beware of pretentious twit." Equally lame are cowboy hats, which are permissible only for someone riding a horse, watching a rodeo or going to a Halloween party.
There is the driving cap, which brings to mind a New York City cabbie, circa 1955 -- something even New York City cabbies don't want to emulate. While a fedora looks great on Humphrey Bogart in the old movies, these days, it's the fashion equivalent of your father's Oldsmobile or maybe Packard. If you're a rabbi, you can get away with it. Otherwise, not.
I've tried most of these options only to feel deep embarrassment in every one. So from now on, I'm wearing a ski mask. Sure, I'll look ridiculous. But no one will know it's me.