think confidence in one's self & what they're wearing is what looks best. I'm not saying wearing food stained wife beaters is attractive, but clean clothes, no matter what your style.. As long as you're comfortable in it & you feel like you look good in it.. That's what you'll look best in.
I've worn really expensive clothes & dresses that were gorgeous.. But they weren't "me" or my style & I didn't feel confident wearing them.. So I felt like I looked awful & most likely did. It's kinda like you inner beauty/confidence shines brighter than anything you can dress yourself in.
Hmmm I don't know... that's a hard one. But I think I'm going to go with a sharply dressed average guy because clothes can really make someone look better and more put together. I love guys with a good fashion sense <3