Well it really depends on your style and what your comfortable in I think if you did a dark wash tight jegging and a cute lose flowing tank top and a really cute sandal pull your hair back into a messy bunn wear some good size stud earrings and accessories like bracelets to compliment your out fit and do a lite girly make-up instead of the intense dark eyeliner( No offense I love my eyeliner to but in this case less is more) but that's what I would do cause you don't wanna look like your trying to hard. But honestly I think if this guy really likes you again it shouldn't matter what your wearing. Just ask him up front don't try to play dress up for him cause then he's going to expect you to do that all the time. Good luck though I hope I helped.