Base the formality of your attire on where you'll be going. For an upscale dinner, wear dark slacks with a long-sleeved, button-down shirt; during colder weather, add a well-made sweater on top. If you're going to a casual movie, wear a nice pair of jeans and a slightly dressier shirt than you usually would. Your first date probably won't require you to wear a tuxedo or a suit, but don't show up in the same outfit you'd wear around the house on a weekend morning. Remember: you want your outfit to hit about the same level of formality as what your date will be wearing. If you're unsure, ask your date what the dress code is or what they'll be wearing.