I started this thread a while ago, but never actually posted my own top 3---likely because I had not formed an opinion yet. I have formed one now, so here are my picks:
1. Rolex Sub (Black)---Everyday/Every occassion (daily beater too). This is the only watch for which I would consider laying out gen money for.
2. Breitling Chronomat (B01)-- For going out to dinner, Dancing, Special Occassions where bling is ok.
3. Suit and Tie (work): Cartier Ballon Bleu (SS)--looks sharp, classic and rich, but without the bling of the Breitling
Runners Up: Rolesium YM (slots in for 2 and/or 3); PAM 111N (or any other non-chrono pam---everyday beater and out on the town watch too); Rolex DJII (suit and tie watch).