My watch "rotation" is (intentionally) pretty small. It consists of:
1. a Sinn U1 that I love, and I wear it just about every day
2. a Luminox carbon fiber SEAL-issue watch that I wear mostly when I'm on ships or somewhere I don't want to risk my Sinn
3. a Shinola that I just like and wear occasionally
What I don't have is a dress watch. James Bond may be able to pull off wearing a Submariner with his tuxedo, but a bulky watch (and the U1 is most definitely bulky) to me just doesn't work with a suit. The Shinola is a little wide (47mm), and it's got a "casual" vibe to it (chrome case with a green face & tan strap). I'm looking for a simple, reserved, dress watch. Stainless with a black leather band. I'd like to keep it under $500, but that's a soft ceiling.
Another watch recommendation thread.