For some reason I never felt the draw of expensive watches. They don't look that great to me. You can have more beautiful ornaments for less -- design for me is key. But then again I don't get diamonds, either. They're just shiny stones. Useful for cutting glass, though. So I guess I'm weird.
Expensive watches are as much, if not more so, jewelry as they are time pieces. A Rolex is a very fine timepiece, but it's also a conspicuous piece off men's jewelry.
If you want some heart attack prices, check out the Patek Philippe watches. I could pay off my mortgage with one off those.
That being said, I wear a Timex or Casio most days.