Dude, no.
I don't want to turn this into a hair thread, but you shouldn't just give up on your hair because you've yet to find what works for you. I was in a similar position back in March, just a generic cut, no styling, didn't really care. I went to a reputable barber (stylist works too) and he hooked me up with an awesome cut that really fit my personality/face, and it's dramatically changed not only my look, but my self-esteem. Think of your hair as another piece of your outfit, right now everything looks fine but that's really holding you back. You'd look way better with some styling of some sort.
As far as your question regarding colors, try navy blue. If you're afraid to try lighter colors, just branch out from black into other darks and gradually take it from there. Blue is great because there are so many different shades of it, you can literally find the exact one that works for you.
DKNY has a pretty solid cheap dress shirt. Macy's retails them at $60 but you can always find them for $30 on sales. For more casual I'd recommend J. Crew and Banana Republic.
Hope that helps.
Good. I've been eyeing a down vest of theirs since forever.
