Rule 2: Wear a tie when you're asking for money. In the days of Mad Men's Don Draper, business attire was simple: Suit, tie, hat, and polished shoes. Nowadays the office looks more like the cantina in Star Wars, with slackers and dandies breathing the same filtered cubicle air. Hence the ongoing confusion: Should I wear a tie to this meeting? It's simple: Wear a tie whenever you're trying to make money gravitate from another person's pocket into yours.