Orochimaru - He's the only person who visibly uses makeup.
Seriously, I'd say Kakashi - the face mask is one of the few articles of clothing in the entire series that actually adds anything to the show - a sense of mystery.
I think Kurenai is really stylish, iht might be just me but i liked her outfit. and i liked Ino's too they were both different, for a lack of better words.