I inherited a Rolex when I was in college. Never got the rub about being spoiled on my first few jobs. (On a side note, it's actually a good thing for employers to view you as wealthy because then they think you won't be totally subservient to them like say, a working or middle class lad trying to pull his weight, and will think of you more as equals.)
Anyhow, it depends on what you want. If you like something that looks classy to be wearing a suit all day, you'll want a Rolex lookalike watch (Seiko makes a few for say, $120-160 methinks). If you like something more practical, you might like something like a Victorinox Swiss Army watch
. I have this and a Nike sports watch I bought oh, 4 years ago, and they're the watches I use most of the time. Rolex is for the special occasions.