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Want to know what to wear on a date? Well there's plenty to choose from vinyl mini skirts, to red-hot dresses, sky-high heels to cool biker jackets. A girl who is demure, a tad old-fashioned but self-sufficient will attract him. pay close attention to hair styles that are short, manageable and stylish and short fingernails that are unpainted, hot pink, flip flops when you're in public with him). Don't wear jeans of any sort, flip-flops, shorts, fishnet stockings, wild makeup, that the biggest turn-off is a girl showing up for a date with wrinkles in her shirt.