Most of the people here are missing the point.
If you're going to wear a watch to impress the most people, it doesn't need to be a good timekeeper. It needs to shout "MONEY LIVES HERE!" to as many people as possible.
Rolex, Cartier, Chanel, and Louis Vuitton do the trick for this. Rolex is the obvious first choice as it hits the trifecta of status symbol, retained value, and excellent timekeeping.