Very smart :) When people see your success and you're trying to sell them something, they will always assume you're trying to rip them off.
As for the discussion, I usually wear what I feel like wearing at that time of the day or if I'm teying to match outfits. Most of my watches are divers, so I just pick whichever one I find interesting. Lately I've been wearing the Seiko SSC813 very often.