1) Daily watch
Rolex YG Daydate 22838 Black dial
2) watch for business occasions where you wear a blazer or a suit, and want to go low key, look like an average Joe.
Rolex Blue Dial Skydweller .
3) a watch for black tie events where you interact with wealthy people. Even if you don't attend those, imagine you do. It would be an elegant watch.
Patek Celestial Grand Complications 6104R-001
4) a watch to show off. One that says that you made it. A watch you wear in Monaco when hunting for a young 'un to join you on your yacht.
Richard Mille McLaren Carbon TPT RM 011-03
5) a wild card. A watch that doesn't fit in. Something totally different
Jacob and Co Astronomia Opera Godfather # OP110.40.AG.AB.A