The Littlest Dandy (GQ)

America's most stylish 8-and-a-half-year-old, Arlo Weiner, reveals his fall style secrets.

Arlo Weiner, GQ's youngest style correspondent, recently started third grade. If you haven't been following Arlo, he's the natty-beyond-his years son of Mad Men creator Matt Weiner. Perhaps inspired by a summer spent at Shakespeare camp ("Talking Shakespearean is really fun."), Arlo's recent look sits somewhere between a court jester, the Mad Hatter, and Michael Corleone when he's pretending to be a Sicilian peasant. This is what we love about Arlo: The kid isn't afraid to mix and match—or mix and not match.