32. Woody Allen
The important thing to note here isn’t just how well Woody has aged into his personal style, but that he can be a style icon for both you and your pops. His look is simple, worn-in, and pretty ordinary, but somehow it’s still unmistakable. And we don’t need to go through the dude’s whole oeuvre to prove that he’s a G (for genius), just trust us, and if you haven’t seen it yet, watch Manhattan. Now.