Expensive watches are cool, but I'll never really need or be able to buy one. Timex is fine with me.
Here are the two I wear nowadays (besides my heart rate monitor, but that's only for running).
An old Fossil chrono that my wife bought for me for our first Valentine's Day as a couple. It still looks great, but most of the chrono dials don't really work. That's OK. I only really use the main dial.
A Timex Easy Reader I got at Target a few months back. Looks great, works great, cost less than a meal at most restaurants.
For the straps I have, see Watch Straps. I usually have the orange and blue stripe on the Timex and the solid blue on the Fossil. I need to switch it up more often.
Speaking of Timex and Target, I was at Target today and saw the Timex Weekender watch. I think they're great, and they come with a nylon strap already, instead of the crummy fake leather that came on this one. If I were buying a new watch (not any time soon), this is the one I would go with. Looks good, and under $40.