How do I get over the loss of confidence I have?

If you look good in them, then it's a plus. But if they are not his cup of tea, he has probably seen you before wearing something he liked better, and that image is certainly not going to suddenly be erased now. So why worry? Variety is good. You won't know what he likes if he never sees you in different things. Keep in mind some guys (not many, but some) can be bad at giving compliments. Maybe he doesn't say much and you think he's unimpressed. Then one day out of the blue, he asks “why don't you ever wear those khaki shorts anymore? So, go for it.

I hope that you know that a guy should like you for who you are and not what it is that you are wearing. Of course you will want to look nice and I am sure that you do. But what ever you wear you will look better with confidence.

Omg haha I do the exact same thing. I pick out a really figure-flattering "hot outfit" the night before school and then after I get ready in the morning I think "damn I am so going to play with this guy today". I don't even think he cares that much but as a girl its just something I do. I know this doesn't answer your question but I just had to post this.