Now I agree with the wearing it right/matching clothes yadda yadda, but some people (you know the ones) need to knock it off.
Aside from that, I'm not much of a hat wearer.
The only hat that I've worn recently was this (or something like this):
But only because A) it was really really cold and B) it made my girlfriend laugh.
EDIT:
Also I realised I didn't really comment on hats as an entity. I guess what I think can succinctly be summed up as 'don't wear a hat because it's a hat'.
Don't wear a hat because you want it to be your thing. Don't aim to be 'The Hat Guy,' because that name will only stick when said with a derisive chuckle. Wear it because it looks good - it actually complements your clothes/head (seriously never underestimate the effect your head can have on a hat - I wore a fedora a couple times (misspent youth) and had to quit because it made my massive head (more specifically face) look like a fucking balloon). Anyway that's my tuppence on the matter.
DOUBLE EDIT: Do I get some kind of parentheses prize?