The driving cap (or flat cap) and newsboy cap (the floppier cousin of the driving cap) do not have the best reputation in the fashion world. They've been misused too many times, mostly by celebrities in the 1990s and grandpas who don’t give AF, and now it seems like the only guys who wear them are the diehard fans—Farrell, Pharrell, and a few others. Here’s the thing, though: These hats have their merits. They walk the line between a baseball cap and a fedora quite nicely and are flattering on a lot of different face shapes. We encourage you to give one a go—just as long as you observe these four styling rules.
It should never be floppy, or weirdly too small.
It should fit you like a baseball cap with some extra fabric on top. That fabric should be minimal, never touching your ears or flopping over to one side. If you look like Chef Boyardee, something’s gone terribly wrong.
Fall is the season to wear one.
Don’t wear one with a T-shirt and Rainbow sandals in June, and don’t wear one in the dead of winter when your head really deserves something more substantial. Now is very much the time.
Wear it on busy, errand-running days.
On a Sunday afternoon, a driving cap or newsboy cap will keep you from looking like a gym rat, while still checking all of the boxes that your go-to baseball cap does. This is the right time and place for the thing—a wedding, on the other hand, is not.
Don’t wear it with suspenders or other old-timey things.
Beware of getting too into the Mr. Autumn Man thing, because you could end up looking like you’re in the movie Newsies. Don’t be afraid to edge the look up a bit with black, urbane stuff.