I personally have a strong affinity towards the Issey Miyake watch line. Their not swiss and (mostly) quartz, blasphemy, I know, but they do look really cool! The Twelve and To are the most modern IMO, and the Insetto has a nice steampunk feel to it, but costs $1000-3000. They aren't sold outside of Japan, but there are some retailers floating around.
Issey Miyake
As vbarrett said, the Seiko monsters are really nice (and impossible to kill) as are their knights, samurai, and dive watches (esp on a nato strap).
And PMWF has a few sub $1000 top 20 lists PMWF