Look you’re going for: Like you’re an outgoing gent who cares, but not too much

You know you're about to go on a date with an outgoing, free-spirited individual and you want to show off your pipes—easy champ, we're talking about your singing ability. It's a great way to break the ice and to show that you don't take yourself too seriously. So you definitely don't want to dress like you're in a barbershop quartet or like a street performer. A nice sweater with a slim-fitting top underneath for layering will keep you warm whilst crooning "Cold As Ice." Slim black denim is basically a prerequisite if you plan on delving into "Thunderstruck," and a pair of Chelsea boots keep it classy as you air guitar and heel stomp across the stage. This basically leaves her without reason not to ask you to "Be My Lover."