Most Helpful Guy
Kylek, wear something that is comfortable because if you don't look comfortable then people will pick up on that. Like if you don't like wool sweaters because they are itchy, then don't wear them.
You could also wear something that gives you confidence. If you know you look good in a button down shirt then wear it. Confidence will go a long way when it comes to attracting someone.
If you have a gay friend, sorry for the stereotypes but, have him help you pick something out. They have better fashion sense then I do and don't mind helping you out. I just wouldn't agree to let them watch you change.