I like to start with a pair of well worn jeans- not too shabby, not dirty, no holes, with a chunky belt. A fitted button up shirt untucked, with a sweater layered on top, complete with loosely tied tie. Throw in some tousled hair, some chuck taylor shoes, a slight smirk, and I'm smitten!
(Don't get me wrong, I like a well dressed man just as much as the next girl- but a boy giving off an artsy, music, outdoor loving playful vibe gets me every time)