I'm definitely of the watch-wearing generation. 
Mine aren't terribly special, though. The wristwatch is my everyday workhorse, a garden-variety Bulova, acquired when a fun-loving friend flung it at my head as I was working (long story, but I caught it in mid-air). The pocket watch was a "gift to myself" after a massive work project for which I received a nice bonus (after finishing a truly ridiculous amount of work on time, no less). It's also kind of a nod to one of my grandfathers; I wasn't very close to him, but I did remember his old, and very well-worn pocket watch. It only comes out if I have occasion to wear a vest, just to give the vest pocket something to do.
Mine aren't terribly special, though. The wristwatch is my everyday workhorse, a garden-variety Bulova, acquired when a fun-loving friend flung it at my head as I was working (long story, but I caught it in mid-air). The pocket watch was a "gift to myself" after a massive work project for which I received a nice bonus (after finishing a truly ridiculous amount of work on time, no less). It's also kind of a nod to one of my grandfathers; I wasn't very close to him, but I did remember his old, and very well-worn pocket watch. It only comes out if I have occasion to wear a vest, just to give the vest pocket something to do.