If you roll up to a party in a shirt and tie, whether it's a swanky dinner or a raging kegger, chances are most people will ask you where the wedding is. They say you should dress like you're headed somewhere better, and the menswear nerd is perpetually heading to class at some school that is probably referred to as an "academy"—or the set of "Mad Men." Whatever, he doesn't care. That's the beauty of dressing nice—you can pretend like you forgot the fact that you managed to stunt on everyone and act like it isn't a huge deal. "Oh this outfit? I just woke up this way."