What look are you going for on your first date? Don't even think about sweatpants and sneakers; the SportsKid look might make others underestimate your intelligence. And don't say you want to wear a suit with dress shoes either—these days, even blind dates don't require formal attire. Forget those sidetracking sneakers that don’t convey much, and also rule out dress shoes which can make one appear stiff and unapproachable—T-shirts, jeans, plus a pair of stylish casual sneakers—are what truly express the real, approachable you.