Like you, I'm a young guy that has only recently started collecting. I second the recommendation to start with some entry level pieces rather than going straight to a $2000 watch. I started off with two $400-700 pieces. During that time, my tastes have matured quite a bit, so I'm glad I didn't go straight for something higher end. I purchased an Oris Classic and a Sieko SARB075. I would look to the following brands, some already mentioned: Hamilton (esp. Jazzmaster), Oris (esp. Classic, Artelier, and TT1), Tissot (esp. Visodate), Longines (esp. Hydroconquest), Seiko (especially Japan domestic models, like the SARB line, see for example seiyajapan.com), and Stowa (esp. Marine and Antea). If you're interested in dive watches, there's a bunch of great boutique dive watch makers right in the $500-1000 range, see the WUS dive forum.
I would also recommend trying to learn more about watches in general. A lot of this can be picked up from reading threads on WUS and elsewhere on the internet, even Wikipedia. Learn about different kinds of movements: quartz, mechanical (manual and automatic), and more exotic movements like the Seiko Spring Drive. Learn about ETA SA, the major Swiss supplier of movements. It's also fun to check out some of the iconic higher end watches, like the Jeager LeCoultre Reverso, the Audemars Piguet Royal Oak, the Rolex Submariner and Datejust, the Blancpain Fifty Fathoms, the Patek Phillipe Calatrava, the Vacheron Constantin Overseas, and so on. You might find a future "grail" or two in this bunch.
Happy hunting.