Why it’s cool: The Rolex Day-Date has been a classic since it debuted in 1956. It was the ultimate dress watch, loved by power brokers including Presidents Johnson and Kennedy, which is how it got its nickname (the President). It’s characterized by its roll-linked bracelet, day at 12 o’clock, and date at 3 o’clock. My favorite reference is the well-balanced 1803 from the 1960s, with a pie pan dial and stick indexes. The only thing to note about the 1803 is it’s a non-quick-set date, which takes FOREVER to set if you aren’t wearing it every day. There are three ways to get past this, including an excellently lazy solution, which is to wait an entire month to wear it after it’s stopped, so you can pick it up where you left off. Alternatively, set the day and date between ten and two o’clock. Or just buy a newer reference with a quick-set date, for instance, the 18238 launched in 1988. With the later references like the 18078, you get stuff like bark-finishes which are niche but very cool.