also, post some links of some really cool shoes plz!
Most Helpful Guy
Certain styles work best for certain people SO, You know what works awesome? Go to stores you like and ask cute girls what they think of certain clothes you pick out. You can start with employees. And you don't even have to pick anything out. Just ask them what they think might look good on you. It's not strange to ask them. It's there job. So you don't have to worry about sh*t. Then, if you're comfortable with it, ask random girls that don't work there. Girls LOVE to help guys pick out clothes.
I do this almost every time I go clothes shopping, except when I already have an item in mind. It's great because you get help picking out clothes, PLUS you get to talk to cute girls, which is good practice. I haven't met a guy yet that doesn't need a little practice talking to girls.
As for Express.. that's my Go-To store for button ups, damn it! Hah. They offer a lot of items that don't have their logo printed all over them, so you don't look materialistic.
Oh and one last thing... Rock t-shirts make you look immature and childish?!? You're killin' me! I wear t-shirts I've purchased from concerts often. Add the leather jacket idea from one of the other comments here and you're golden.
I'd throw in a motorcycle for the full effect.. Haha.
Good luck, boss.