I recommend the classic....NOTHING.
Both should wear matching dresses. same type of make up. It should be fun!
Just wear something apprapriate for girls your age. Try not to stand out from the crowd, but something that shows off your best features.
Long lean men's pants, kind of dressy, a shirt that's kind of unisex, and a sport coat. If you want to take it over the top, find an old Fedora for a hat.
Depends where you're going.
Also work on your English.
Are u sure you are 22 years old? What grown woman asks this kind of question? The problem I have with your question is that you say you are going on a date with a boy wearing a girl dress? Do you identify yourself as something else?
You better put on a nice dress, makeup, and spend some time on your hair. Can't let your man out do you can you?
Wear something with pockets, for cab fare.
blue jeans, camouflage shirt, and combat boots . . . sans make-up . . . a lovely couple.
jeans, t shirt, boots
Wear something he will like, but conservative, so he will look better than you.