One of the truly iconic (and I don’t use that word lightly) calendar watches of all time, the Rolex Day-Date got a huge update in 2016. Sure, the watch still looks the same, but under the hood of the 40mm version is the new caliber 3255, which features Rolex’s new Chronergy escapement, which is both very energy efficient and resistant to magnetism. This movement is also the first to be tuned to the new Superlative Chronometer standard of +2/-2 seconds per day. More on the difference here. Sadly, the updates did not make their way into the 36mm version, but even in the bigger size this is about as classic as it gets. This is the calendar watch for the person who’s a boss and knows it. 

$34,850 (as shown here),