Patek Philippe from Hodinkee Annual Calendar 5205g ($53,925)
Collecting watches used to mean buying for life—and your choices were mostly limited to
very new watches or very old ones. But now, what used to be a sketchy gray market for pre-owned watches—that is, lightly worn pieces produced after 1990—has turned into a low-stakes way to build (and rebuild) your collection. Hodinkee, the watch media brand, acquired pre-owned platform Crown & Caliber in 2021. That site, along with peers like WatchBox and Watchfinder & Co., have made it easier than ever to do the hardest thing in watch collecting: painlessly buy something you're into without fear of getting scammed. Reams of historical pricing data and teams of authenticators, along with return policies you won't find on the gray market, mean that you can trust in what you're getting—even if you're picking up this Patek Philippe. All the better, dipping into this world gives you the freedom to think of your collection a little more…fluidly. “There are watches you're gonna engrave your name on the back of and never get rid of,” says Russell Kelly, Hodinkee's chief commercial officer. “And then there are watches that come and go.” The rise of pre-owned means that the latter will find a happy home—by which time you'll be onto your next watch.