To see how popular watches still are, one can go to eBay and do a search for ant watch brand, Casio, Timex, Citizen, you name it. Look at the bids. Almost every watch will have bids placed and or but it now options. I bought ten watches on eBay over this past year, all 1955-1980 windup/automatic Timex watches that still run and keep great time.
Or you could go to Tourneau and check out a fine selection of dozens upon dozens of watches selling for 4 to 5 figures. Plenty of people buy watches and wear them.