I love watches that exude quality and elegance, that do not shout "look at me, I'm a Rolex!" No one likes a showoff, don't be that guy. You're (probably) young. You're (hopefully) successful. You don't need to rub it in other people's faces. BUT, that doesn't mean you can't treat yourself.
Here are a few favorites:
Cartier 21 Chronoscaph $3000-4800: Perfect for the casual outing, but pairs just as well with the suit/tie.
Graham Swordfish Chronograph: $6000-10000: A big boy version of the Cartier.
Louis Vuitton Tambour Chronograph $15200: The leather band makes this watch perfect.
Louis Vuitton Tambour Mysterieuse LV115 $265000.oo (?!) - Wow.
Ok, so they're all a bit pricey, here's one that won't break the bank:
ESQ (by Movado) Stratus ($450): The look of a Breitling, at a fraction of the cost.
And of course, the requisite BR item:
Canvas/leather Banana Republic watch that I found on eBay for $7!
If money were no object, I'd own 'em all!