There are more grey areas than Moscow in winter when it comes to assessing a vintage Rolex. It’s like a giant, room-sized 50 year old puzzle with mushy, tattered pieces, none of which fits perfectly. But if you’re into vintage Rolex, and you’re into deep research and esoterica, you’ll freaking love searching for the right vintage Rolex.
They say it’s all about the journey, but I disagree; the destination is absolutely marvelous. You are wearing a stunning piece of history on your body that contains a rich collection of stories you can only dream about. And now, you can layer your own stories on top!

But imagine if you arrived at your destination then, through further research, determined that you vastly overpaid. Or worse, that you bought a “frankenwatch”, one assembled with original components from various watches. Oh you’ll tell yourself that you still love the watch. But there will always be that ugly knobby mole right in the middle of the dial each time you look at it. So let’s try our best to keep that from happening!
Although most of what we’ll cover will apply to Rolex sport watches, the most tips will apply to all Rolex vintage watches. The big caveat is that there’s no substitute for having the watch, 1) in hand; and, 2) examined by an experienced vintage watchmaker. Fortunately, dealers offer a return policy. Unfortunately, you have to move fast as it’s generally 3 days and it’s usually “return if not authentic”. A Rolex with a service case is authentic; but it also severely depreciates the value.
This series of articles will cover the superficial, “easy” things you can assess before you buy or even before you post on the Vintage Rolex Forum, hoping for feedback from one of its many experts. You may not learn enough to disqualify a watch from purchase but will definitely learn enough to ask the seller more educated questions and possibly hold back from pressing that “Buy Now” button without help from an expert.

Of course your best route will always be to “buy the dealer” and there are established and reputable expert dealers around the world. But you still need to do your homework as they can miss things. One quick example: after a week of scanning the pictures of a specific Submariner from a very well-regarded dealer I finally noticed that the pearl, or pip, in the insert looked whiter than the buttercream tritium markers and hands (don’t worry, we’ll go into that).
I asked the dealer who then confirmed it was a luminova pearl rather than tritium. This doesn’t seem like a big deal but a new old stock tritium pearl cost me $300. Omissions or mistakes from reputable dealers are just that – mistakes and no reason to be bitter about it.
The important bit is that I knew enough to ask.
Buyer's Guide:
Hereunder the updated list of chapters to this article. Note that Future articles will cover dials, hands, and luminous; bezels and inserts, crystals and crowns, bracelets, and more esoteric minutiae that is fascinating to people like you and me. Please note that links to the individual pages will be updated over time. Make sure to bookmark this page, this is going to get really detailed over time.
Part I: Vintage Rolex Watch Case Details You Need To Check Before Buying