6 Vintage Rolex Watches That Offer Surprisingly Good Value

The stage is set: You’re killing it at work. You’ve got some extra cash. It’s time for a nice watch. A Rolex watch. There’s just one problem — or three, rather. Unprecedented demand, a global pandemic and limited production mean there’s too few watches to go around.

Your best bet? The preowned market, where supply’s aplenty and even deals await. Here are the tips to dial in your search.

Think small, literally. There’s more to Rolex than Submariners, Daytonas, and GMT-Master IIs. There’s a mind-blowing variety of options, many under $5,000, in the 34 to 36mm range. Forget the small-watch stigma and check out 36mm Datejusts and vintage 34mm Oyster Perpetuals. If sub-40mm is good enough for Ryan Gosling, it’s good enough for you.

Study your target. The Rolex world — vintage, preowned and new — is rife with fakes, “Frankenwatches” and all sorts of shenanigans. Once you’ve found a model you want to buy, study up on what it’s supposed to look like. Watch YouTube videos, go into boutiques and stores and begin handling watches. Speak to experts, buy some reference materials. This part might seem tedious but it will save you a lot of trouble when it’s finally time to buy.

Buy from a reputable seller. Can you score a deal off a random internet sale? Sure — but it’s risky. Instead, the best bet for newbies is to start with established dealers. Two great places to start are Eric Wind from Wind Vintage and James Lamdin from Analog:Shift. These guys are consummate pros and exploring their offerings will help you learn what’s worth buying.

Take your time. Don’t rush into a purchase and buy the first watch you see. Look at 15 Datejusts if necessary, or at least two or three — that’s half the fun! Aim for a piece that won’t incur extra service or other costs. It’s much better to spend a bit more on a watch that’s already been properly serviced and is in good condition. Buying a screaming deal on a “project” watch is not for beginners.

Wear the living hell out of it. You earned it! Just know that preowned (and especially vintage) watches need extra care. Don’t take it in the water unless it’s meant for that express purpose. And only after you’ve had it pressure tested. Also understand that at some point, it will require service, and that won’t be cheap. The same is true of a sports car, a home or anything cool worth buying.

Need help settling on a model to set your sights on? Here are some models and ranger that hit the sweet spot: timeless enough to wear, common enough to be affordable.