Dress to impress by staying away from cut-off shorts, run-down sneakers or ripped up denim. It doesn’t matter how expensive your jeans are, if they are shredded, your date will wonder if you pulled them out of the bottom of your laundry basket. In general, most men dress pretty casually from day to day, so put a little thought into your outfit and show some class by pairing a fitted button-up shirt with a dark pair of jeans.