A guy typically does not care what you wear on a date as long as you look good. If it means wearing jeans, a skirt, a pink tu tu or boxer shorts, then so be it. Although, if you plan on hooking up with the guy there is something to be said about the easy access possibilities of a dress. Jeans (especially tight ones) can be difficult to quickly remove.
Mystery Man
On a date, do guys prefer jeans or a dress? hair up or hair down?
Mystery Man answered this question on March 3, 2010 9:35 AM
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Also, it might be a good idea to not wear a backless tea-length dress with diamond tiara to a rodeo.