I'm fortunate enough to own an Omega Speedmaster Professional after saving up and buying a good pre-owned example earlier this year. I love it, not only because of the timeless design (essentially first released in the early 60's and the design has barely changed since then, except for a few cosmetic differences) but also the history of it (worn on Apollo space missions, worn on the moon, etc).
But I also own a number of other far more affordable watches.
Essentially there are three types of watch movements:
* Quartz - battery powered
* Automatic - has a sort of pendulum inside the watch which, as you move around, winds up a mechanical movement
* Manual - you have to wind it up every day before you put it on
Quartz is very popular but usually cheap to produce unless you go into the more high end types of movement. Generally unless you're talking about a very very reputable brand, it'll have a cheap movement in so probably not worth spending a lot of money on ($250 max).
If you fancy a cheap entry into mechanical watches, then have a look at the Seiko 5 watches. They're very affordable, very well made, usually have a display back so you can see the inner workings, and they do a wide range of styles to suit most tastes. I have the fairly well known Seiko 5 'military' style watch and it works great and easy to regulate the time (automatics and mechanicals are generally far less accurate than quartz but can be adjusted to be pretty accurate).
There are some other good brands mentioned here - Tissot are very well known and have been in business for decades, Fossil watches are kinda cool and Parnis are excellent - I have one myself (which is a bit of a shameless homage of a Panerai watch which would normally cost $6000...)
But it's worth saying after all that, this is just my opinion on things - and really if you find a watch you like, regardless of cost, then just buy it. I can't quite get the mindset of people that buy quartz fashion watches at $5000... but each to their own I guess!
Keep us updated on what you end up buying!