I would like to recommend you check EDF, there's a very very lengthy watch thread that you should read, and then ask your question there and lots of watch experts in the thread.
The EDF thread seems to be mostly balla-wannabe watches. If that's what you're interested in, you're gonna have to open up the wallet a bit more than you indicate.
If you're looking for an everyday dress watch, you can find a good looking Citizen or Seiko (basically the same engineering), or a Bulova. If those are a little pedestrian, you might can find a sharp looking Movado on sale. I prefer a sapphire crystal, but that'll shoot the price up, as well. Check independent jewelry stores such for a well taken care of TAG-Heuer or Omega, as some of them will take them as trade-ins, and are pretty stringent on what kind of shape they're in. I have a TAG, primarily due to the sapphire crystal. I'm pretty rough on my watches. But I was a TAG dealer, and got it for about a third of the retail price.
Also, I prefer a leather band. Most prefer a metal band. That can impact the price a bit.
Your best bet: A forty- to sixty buck Timex is a more durable and better engineered instrument than a Rolex or any other douche-accoutrement you'd throw down a bundle for. Quartz technology is a great equalizer. My best friend's father, who was a well-respected VP of a rather large bank, and is pretty well known in financial circles, told me once that in negotiation sessions, a Rolex (or similar luxury watch) wearer could be pushed around and easily manipulated, while a Timex wearer was all business.