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It doesn't matter what you wear on a date as long as it exudes confidence. Here are seven first date outfit ideas that always make me feel my. I can't definitively tell you what you should wear on a first date, but I can give you a list of things you should absolutely NOT wear when you're. If you're suffering from those all too familiar, I have nothing to wear! jitters, it's time to get acquainted with our "what to wear on a first date" guide for women.