As you date someone more with increasing regularity, the anxiety over what to wear will lessen. That doesn’t mean you should roll into The Dresden in a flannel shirt, but if a chick is into you, how you dress becomes less important to her than who you are and how you treat her.
Warning: There is a temptation, on the part of some guys, to fall into a comfortable rut. Same routines. Same clothes. Same look. Overcome this urge.
Never act, or dress, like you have “won.” Dress like you are always trying to impress and she will appreciate – and reward – the effort.