I am thinking I should go ahead and get a watch. When I was younger, I found metal bands to be extremely uncomfortable (pulling arm hairs), so I've largely stayed away from watches. However, I recently tried on several watches with leather bands and found them to be far more comfortable (and, of course, much classier).
I'm looking to spend $500 or less (which I realize is not much in the watch world). For work, I wear a suit, blazer or sport coat.