Oddly enough, I seem to have good luck with "el cheapo" watches. I bought a "Wilson" watch at Wal-Mart for something like $15 when I was in 8th grade. The plastic band broke and was held together with staples at one end after three or four years, and the other side, the plastic body broke enugh that the band had to be held on with masking tape. But last I checked, which was a couple years into college, the thing was still going strong on its original battery. That's a good six years or so. Good quality battery.
I got a Wenger Swiss Army Watch as a high school graduation present. I wore it for a few years. It's water resistant to 5 ATM, it says, and the set knob requires unscrewing before I can use it to set the time. But I'm not sure how water resistant the two side buttons are. However, the hour hand decided to quit moving one day. I took it to a jeweler and had the battery replaced, and he couldn't figure out anything else that could be wrong with it. The problem was not fixed.
So I bought a Timex Expedition digital watch for $3 or $4 at a Kmart that was closing down. It has a cloth/velcro band that is still good, although the velcro doesn't grip that well anymore. It is still keeping good time and it's still on its original battery. It's water resistant to 100m.
I currently wear a cheap $10 watch that's 30m water resistant but looks a lot nicer than the Timex. I figured that since my job at Radio Shack requires me to look a little nicer, I should have a nicer-looking watch.
I don't go diving, so I don't really need much water resistance, and for some reason quality hasn't been much of an issue for me, even with "el cheapo" watches.