Watches are largely an anachronism. Between our computers, phones, etc there's always something nearby with a clock. My wrists have been unburdened of timepieces for many years now (although I did go through a pocketwatch phase earlier this century).
But there is one watch I've always coveted - the Jaeger-Le Coultre Reverso Duo. This classic design dates backs to the 1930s when a noted polo player needed a watch which could be protected during play, hence the design where the watch crystal can fold over to expose a stainless steel back (pictured here). Although they now make fancy versions in gold and with a second dial on the back for another time zone, I love the original leather band and blank back. My understanding is that the watch gained popularity here in America with up and coming middle managers. They were still spending time on the factory floor but needed to also be appropriately dressed for the corner office. So it was steel side up for blue collar, crystal side up for the white collar. Poetic capitalism at its best.