1) Seiko. Buy yourself a "higher end" Seiko like a Grand Seiko, or even simply a Seiko 5. If you need to class it up or you want to make it look like you spent more money, buy yourself a gator watch band for ~ $200-250. For that money, you could get yourself a couple and have a nice rotation
[I am a big fan. I have a Seiko 5 and a Seiko Diver both on NATO Straps]. Can be had for dirt cheap.
2) Stowa Marine!! How has no one recommended this yet. Flashy enough for a young guy yet classy enough to keep forever. You can get the base model with a polished case and alligator band for under $1000 shipped. This is really what I'd suggest. I'm 23 going on 24 and am patiently waiting to receive mine with a nice Sirtoli gator strap
The end of April cant come soon enough