Left (non dominant) wrist, dial up.
I've got about 50 watches as I'm a bit of a collector, the ones I wear the most are my Omega Speedmaster '57 Reissue (leather strap, retro, casual) and my Rolex Submariner Date (steel bracelet, current, business casual). My beater watch is a Luminox Navy Seal (lightweight, battery, rubber strap) which is a great utility player.
Everyone man needs 3 watch types: Sport, dress, beater.
nice. The Omega is great.
The 3 things I'll ever wear on my wrist are a Timex Ironman Shock, Suunto X-lander, and Fortrex 401. I need a dress watch when I dress up, I suppose, but I usually wear nothing with my suits unless I'm working (Suunto).