Right now I'm going for looks. I'm slightly recovering my social life back, and I am in the mood to get just slightly flashy (in a tame way.)
Obviously, "Rolex" is for the people going for looks/recognition. What do you think of Movado? Overstock.com sometimes has good deals, but you are in the 500-1000$ range. They can be "dressy" and their "appeal" is their simplicity (some people think they are too simple looking with the blank dial with single stone at the 12 oclock position).
If you want something that "Works" and looks "nicer" than a Timex or G-shock, then Citizen would be my first choice since it is a blend of features I like (no batteries, many different models to choose from) and they do not break the wallet (<$500).
Honestly, my progression of watches was:
1. Timex Indiglo (elementary school)
2. Timex Combination Indiglo (analog and digital) (Junior high through high school)
3. Citizen Eco-drive titanium with chronograph (12th grade, College, grad school, and 2 years of work thereafter)
4. Omega DeVille Annual Calendar (my wife's gift to me)
I wear the Omega everyday and my Citizen doesn't get worn at all anymore. My Citizen got me through a lot though and it was and still is a trusty watch. It didn't have a date function, and I realized that I wanted that. Also, I don't want to have to change the date every other month, so, the Annual Calendar suits me now.
Sounds to me like you want a tier higher than Timex, but a couple tiers lower than Rolex/Omega/Panerai/Gran Seiko/etc. That puts you in the 200$-1000$ range. Citizen, Seiko, Movado are the first brands that come to mind. They all have their own unique "design" traits so you can see very quickly which direction you want to go.
You need to go to a store and try them on btw. There were several models of watches that I liked in catalogs and on the internet, but they looked terrible in person on my wrist. The DeVille that I have was ho-hum in the pictures and even 3' away in the display case. However, when on my wrist, it just presented well to my eyes and my wife's. Oh, and never pay MSRP retail. You should be able to get a discount as these things are marked up at least 50% from "Dealer pricing".