Don’t overthink this. If you have to consciously select an outfit for a night out in New York, you are going to all the wrong places. No club in New York that’s worth its salt cares about what you look like (that is, unless you are a complete schlub). At the end of the day, they only care about whether you are rolling with women and are willing to spend dough. If you are rolling with 10 dudes and have bunny ears, even if you are wearing a $6300 suit, not even God could save you.