I didn't wear one for 6-8 years. I got one of the first Timex Expedition ones when I finished Basic in '96. Frakkin' thing has been through at least four wristbands (leather on the ends tends to wear & break) and a new seal and screw on the back, not that it'd matter since the plastic around the buttons is worn. Regardless it still functions alright when it's wet and not sure if I've even had to change the battery. I got a newer version of the Expedition about four years ago to replace that one when it diess (all digital ones have died for me in a couple of years before) but the original is still going. I started carrying it in my uniform pocket so I wouldn't have to keep replacing the band.
Plus I worked flightline for about six years so couldn't wear watches or rings at work. Looking at getting one of those all-web type of bands. The replacement is still on the plastic display stand being used as a desk clock by the computer.
I got my cell phone after I retrained off the flightline so got used to using that for a while.
I now wear a decent analog Fossil one most of the time, I agree it does seem to be a note of interest when wearing a decent one even if it isn't a Rolex. I've had a jeweler or two ask me how much I wanted for it. I also have a Tag Heuer replica kinetic I bought in Turkey for $25. I was curious one day and took it in to a store that sold the real ones to see what the difference was, after five minutes of looking at it the only things he could tell was that the letters were a different color (think they're gold vs white) and the back was transparent. He said they didn't make transparent backs then, although I think I've seen some since with. Another difference I noticed later is it doesn't catch up the day/time if it stops and is restarted like I think the actual ones do.
I used to wear a pocket watch in high school, been thinking of getting another one.
