The styliest guy in the room is also the simplest. If you do not know what to buy, keep it simple: get 1 pair or Rock and Republick (they always fit), and 1 7 for all mankind, get 2 white shirts and 1 black one from J crew. Pack up on Hanes t-shirts. Add a simple stainless silver watch, you are done. Do not worry about the shoes, just keep them clean, and no square toes.