I can't think of too many better ways to waste money with no discernible benefit than to wear a ritzy watch. There was a time when the "status" of a nice watch appealed to me, but those days are over. If I ruin a $50 Timex mountain biking (which I have), no worries. If I ruin a $2K Heuer, my month is pretty well ruined. I also do not find it satisfactory to, as a previous poster stated, service a watch every year!
I wear a Timex Indiglo iControl; I guess if cost were no object I would have a stainless Cartier Panther or Tank watch. My last Timex, which got badly scarred in a velodrome crash, has lasted 5 years and is still working fine, for a whopping $35.