I'm a bit of a watch guy. Basically all wristwatches fall into two categories: quartz and mechanical.
Quartz watches are generally cheaper and are basically always more accurate than mechanical. They run off a battery, and lots of serious watch guys think all quartz watches are created equal. You might pay more money for fit and finish, but basically any quartz watch is exactly as functional as a good old Timex.
Mechanical watches run off springs and gears. They don't have batteries, so they never 'die', unless there's a mechanical breakdown. The tradeoff is they're less accurate, and generally more expensive. High end brands like Rolex, Breitling, etc. specialize in mechanical watches, esp. 'automatic' watches, which are powered by the motion of the wearer's wrist winding a mainspring.
If you want to spend under $200, buy a quartz watch. If you want to go over $500, buy an automatic. After you make that decision, it really comes down to aesthetics.
I generally keep three watches: a big chunky plastic watch (like a G-Shock) I wear for exercising and very casual situations, a mechanical dive watch for most activities, and a slimmer 'dress watch' for things like church on Sundays and when I wear a suit.
Most of the time I wear a rough and ready Seiko SKX007 dive watch like this:
You can pick one up for around $200. But don't feel like you have to spend a ton of money to have a watch you enjoy. I've had many Timexes which gave as much or more enjoyment as watches costing many times more. It's just like pipes-- some guys have huge collections of old Dunhills, and some have two cobs and some Carter Hall. Both guys enjoy their pipes, and one isn't a superior experience to the other; it's just different.
