The Two-Watch Vintage Rolex Collection: The Expected And A Surprise

There’s absolutely nothing wrong with modern Rolex watches. Well, aside from the fact that you cannot get them from your local boutique and secondary prices are still well over retail. But while that’s annoying and there have been countless articles about the phenomenon, I haven’t really been affected. Why is that? It’s because I’m a dyed-in-the-wool fan of vintage Rolex, and I prefer to put my money into watches that aren’t still in production! But where to start and where to end? Everyone will have their say, but I have come up with two vintage Rolex watches that could leave an owner with a no-regrets collection.

That’s right, it’s another Rolex article, but we aren’t joining the chorus with yet another complaint about availability or secondary market pricing this time. Today, vintage Rolex is back in focus, and the idea was to choose a tight, two-watch collection. Why two? Well, it allows for some level of differentiation. It also keeps a collection tidy and wearable. As far as inspiration, I looked no further than my own wrist as the arbiter. If I consider the past 12–24 months, it’s very easy to see which vintage Rolex models (and, frankly, these watches dominate time on my wrist) I wore most.

Vintage Rolex is insanely wearable

Seemingly, in the world of watch collecting, there are vintage folks, modern folks, and vintage folks who accept modern watches. I rarely find a modern-watch lover who accepts vintage watches. They’re usually afraid of these watches (for good reason at times) or find them inferior/fragile versus newer watches. What I’d like to mention, and I’ve said it before, is that vintage Rolex is insanely wearable. If one can deal with an acrylic crystal, everything else feels solid and contemporary. The watches can be tested for water resistance and serviced easily. Friends who moan about the more rudimentary bracelets simply don’t know what they’re missing. Even if the bracelets were lighter, they were leagues ahead of their competition in terms of comfort and durability. Just try living with one for a while. It’ll make the newer models feel needlessly heavy and inarticulate by comparison. With all that being said, what did I choose?

The Datejust 1600

It’s probably no surprise, but my first vintage Rolex pick is the wildly versatile Datejust 1600. Before deciding to pick it up at the end of 2021, my tastes tended toward sports models. However, I felt the desire to try a Datejust. For me, the smooth-bezel 1600 was a nice compromise as it isn’t quite as ornate or dressy as models with textured bezels. Yet, the watch emits dressier vibes. I’m here to tell you that this 36mm steel watch on what just might be the most sublimely comfortable Jubilee bracelet has stolen my heart. There’s no other way to say it: I love wearing this watch.

A testament to its absolute wearability, the vintage Rolex Datejust 1600 has been a partner on lengthy trips both for business and pleasure. It feels at home with a pair of shorts, formal garb, or whatever the day demands. It’s somehow luxurious and rich-looking, but it also flies under the radar. These days, when people think of Rolex, they likely have a chunky timepiece in mind. The 1600 is lithe and, for a Rolex, downright elegant on the wrist.

Blue is great, but there are other lovely choices

I lucked out with this blue Datejust 1600 that dates to 1975. The condition of both the case and, most importantly, the dial is superlative. I’m sure that any model with this reference would be of interest, but there’s just something about a darker dial in fantastic condition. I say that because that’s the challenging part of these watches. The small tritium lume plots either tend to come loose or eat into the dial lacquer. The cases are also a challenge because they lack clear, beveled edges like many of the sports models. A quick look at the lug holes for rounded edges can help show signs of unruly polishing.

The good thing about this model is that it’s not a bank-breaker. Prices have risen over the past couple of years, but they have stagnated recently. Savvy buyers may be able to find something worthwhile for under €5,000 while great examples can run over €6,000. Still, for a vintage Rolex, that’s not bad, and it’s not likely to depreciate over time. The Datejust still looks largely the same, and that has kept these vintage models relevant despite their non-quick-setting 1570 movements. Also, note that overall availability for these watches isn’t an issue, but finding a great one takes a lot of searching.

In summary: this could be a one-watch vintage Rolex collection

The Datejust 1600 is so good, so comfortable, and so easygoing that it could easily suffice as a one-watch vintage Rolex collection. In fact, if true sports models aren’t your thing, stop right here and save a ton of money. You won’t be disappointed, and you’ll have a great watch that will last generations.

The Sea-Dweller 1665 “Great White”

Most would guess that something like the Datejust 1600 would make the cut for a two-watch vintage Rolex collection. I’d bet that literally no one would pick the Sea-Dweller 1665 “Great White” as the second piece. The Submariner, GMT-Master, or some sort of Explorer are far more popular than the oddball Sea-Dweller. So what gives? I’ll do my best to explain.

None of us younger folks can go back in time and know what life was truly like when a dive watch was truly necessary as a tool. However, when I speak to those who dove during the ’70s and into the early ’80s, there was one watch brand that was seen as far more reliable than any other. If you guessed that it was Rolex, then you’ve at least paid a little attention to the article thus far. With that in mind, the Submariner would be a perfectly suitable choice, but I like the fact that Rolex created the ultimate professional expression of a dive watch with the Sea-Dweller 1665. Therefore, it reigns supreme as my choice for the second watch in this collection.

Ugh, I love to wear this watch

If I’m in the mood to wear a brawnier, tough-looking watch, the Sea-Dweller 1665 is almost always my choice. It’s thick (>17mm!), but it wears as only a vintage Rolex 40mm case can. Plus, just look at that flippin’ crystal! It’s like a porthole out of a Jules Verne novel that magnifies things head-on and disfigures all of the dial elements when viewed from an extreme angle. It’s just so purpose-built! Then, in a world where everyone gloats about “Easter Eggs,” the inscribed case back exudes this “not for public consumption” type feel.

There’s just so much to enjoy on the Sea-Dweller 1665, such as big, fat lume plots against a matte black dial. Then, view the watch from the side and digest the taller bezel that aids use when wearing gloves (those would be of the “winter” persuasion for me at best). The watch comes on the 93150 Oyster, which still ranks as the greatest sports bracelet in the history of watches. Yes, most modern watch companies should bow and seek tutelage from this amazingly comfortable concoction. For those who hate the Cyclops, the Sea-Dweller even delivers the best of both worlds because it serves up a date under that T39 tropic crystal.

A more challenging vintage Rolex to buy

The vintage Rolex Sea-Dweller 1665 that I chose is the “Great White” model that came after the famous “Double Red.” Mechanically, the watch is the same as it uses the automatic caliber 1570 and even has a small, simple-looking helium valve on its side. However, the Great White is significantly less expensive. On the other hand, it was produced for a fairly short period (1977–1983) and likely not in the same quantity as the Submariner. Finding an example is easy, but finding one in nice condition is challenging. The tall case and crystal were likely targets for dents. Consequently (and sadly), many have been polished or contain service crystals with defined edges. I think it’s worth holding out to find a lovely model with a warm patina, honest wear, and the right crystal. These days, expect to pay north of €25,000 for a nice example. That’s a lot of cash, but one could easily spend that much on a vintage Submariner. Yes, the Sea-Dweller is more of a specialized watch, but that defines its stealthy charm.

In summary: forget the usual suspects and go for the big gun

The Sea-Dweller 1665 “Great White” isn’t cheap, but it has escaped the focus of mainstream vintage Rolex collectors up until now. To me, that still makes it a relative (yes, very relative) bargain versus the other heavyweight sports models. Perhaps the general lack of coverage of this model has kept it out of the limelight, or the fact that it isn’t found on most vintage dealers’ sites has suppressed its popularity. Whatever the reason, the shy status can be your gain. Trust me, these wear beautifully, and it’s nice to sport a vintage Rolex that most don’t own.

Vintage Rolex — Oddly practical

Look, we all know that vintage Rolex can be a scary proposition, but if one buys from a reputable seller, look forward to many years of satisfying ownership. These watches can be worn every day, and while I don’t swim with them, there are plenty who choose to do so. They’re rugged yet refined, a balance that current Rolex models seem to have lost. The other nice point is that these watches are fairly liquid, so selling them is relatively easy if a lengthy romance isn’t in the cards. I chose two watches that I could easily wear all the time. What would you select as your vintage Rolex pair?