The 10 Best Vintage Rolex Watches To Collect

By Charlie Dunne

I often hear the question “What are the best vintage watches to collect?” While we love and collect a wide range of manufacturers, Eric Wind and I are especially confident recommending vintage Rolex watches to new and established collectors, for a wide variety of reasons. You can wear them just about anytime/anywhere and we firmly believe few options are superior to the robust quality found in vintage Rolex watches. This can be found in certain aspects such the case quality and construction, as well as the fact many of these models can be readily made water resistant despite being 50+ years old! In addition, it is not uncommon that we will place a vintage Rolex on a timegrapher to discover the accuracy and amplitude are impressively high despite no service history. Contrary to what the Swiss watch industry might claim, the durability and performance of vintage Rolex is superior to many contemporary offerings from so-called “haute horlogerie” manufacturers. For now, we are excited to share ten options to seriously consider for vintage Rolex watches:

1) Rolex GMT-Master Reference 1675

The GMT-Master reference 1675 is such an obvious way to kick off this list, and for great reason! As I wrote in my article ‘Collector's Guide: The Rolex GMT-Master Reference 1675 In Steel’ “There’s no other watch like the Rolex GMT-Master reference 1675. 1675s are incomparable to any other watch as the variety of dials and beautiful bezels can be profoundly different across years of production and manner in which they have aged over time.” They are simply breathtaking sports watches. It is one of the most recognizable watches on the planet. Despite being able to recognize the watch from a mile away, I am always eager to initiate a conversation with the wearer about their GMT-Master and get a closer look at the dial, bezel, and case! It is just a special reference.

The GMT-Master reference 1675 is not an uncommon reference to see at a collector meetup, so you aren’t looking at the rarest model in the Rolex catalog. However, finding an excellent example that has not been messed with could certainly be a trophy watch for collectors at any level. Whether with a gilt or matte dial and a vibrant or faded bezel, the 1675 is a romantic watch that represents the best of sports watches. I consider my 1675 the cornerstone of my watch collection and am thrilled each time I wear it.

2) Rolex Oyster Perpetual Reference 1002

Scaling back from the price for a reference 1675, the Oyster Perpetual reference 1002 might be the quintessential entry-level Rolex watch. The reference 1002 packs a major punch at 34mm. Each watch was tested for chronometer certification alongside the heavy hitters from the brand. These OPs are both charming and chic. The dial variants are a complete spectrum of colors. One could even justify having different 1002s in their collection. For thick-wristed individuals, these may be a bit too small. However, I think these look fantastic on a wrist as big as approximately 7 inches in circumference.

3) Rolex Air-King Reference 14000

Another favorite reference at Wind Vintage, regardless of price, is the Air-King reference 14000. We consider it the last great Air-King as is much more attractive than the current Air-King offerings from Rolex. The Air-King reference 14000 wears a bit more favorably compared to the predecessor Air-King reference 5500 as well as the aforementioned 1002 because of the larger lug-to-lug dimensions. These are among the final Rolex watches to be released without chronometer certification and yet we often find they perform better 25+ years later without a service on a timegrapher than the top product lines in other manufacturers. For under $5,000 you can get an extremely nice example that will provide a lifetime of enjoyment! Honorable mention for the Air-King reference 14010 that is identical to the 14000 except with the addition of a steel engine-turned bezel.

4) Rolex Submariner Reference 5512 & 5513

The Rolex Submariner is an iconic sports watch, and the reference 5512 and 5513 are two of the most collectable references within the model’s history. The reference 5512 entered the picture in circa 1959 as the first Submariner with crown guards (the earliest examples had square crown guards, before going to the eagle beak crown guards, then pointed crown guards, and finishing with rounded crown guards). The 5513 would be introduced shortly after in circa 1962 (with pointed crown guards followed by rounded crown guards). These references certainly played a vital role in establishing Rolex as the preeminent tool watch, and 60+ years later, the watches remain outstanding timepieces.

The Submariner is very similar to the GMT-Master in that it is such a recognizable watch. The 5512 models were equipped with chronometer-grade movements, while the 5513s were the more budget friendly alternative within the Rolex catalog. The 5512 would remain in production from 1959 until circa 1979, while the 5513 was offered from 1962 until circa 1989. These longer production runs with higher output of references can be a key component on why a reference is appreciated by collectors. Some collectors have an approach to search for the rare models. While I love an uncommon timepiece, I would personally suggest approaching models with long production runs, as the opportunities in finding top condition examples is more obtainable. “The biggest shift in collecting over recent years is prioritizing condition above rarity” Eric Wind stated on the subject. “That’s not to say that rarity is unimportant, but rare models - say with a reprinted or distressed dials or in rough condition overall, are not sought after like they were 20 years ago”. In addition, the nuance within the models and evolution is a subject that adds to a wider appreciation in the collecting scene.

5) Rolex Oyster Perpetual Reference 1018

Yes, I am still obsessed with the Rolex Oyster Perpetual reference 1018! It was my first Rolex, and I strongly believe it is among the coolest Oyster Perpetuals ever produced. A while back, Eric helped me find a spectacular example which currently resides in an amazing collection. These watches are incredible and wear so nice on the wrist at 36mm and 43mm lug-to-lug. One strong recommendation: Do not settle for a service dial! I have yet to get my hands on a gilt black-dial variant, but when I do I’m sure you will hear all about it. To learn more about this watch, read my Collector's Guide: Rolex Oyster Perpetual Reference 1018.

6) Rolex Datejust Reference 1600, 1601, 1603, 16014, 16030, & 16220

The vintage Rolex Datejust is truly a classic watch. It plays to both a dressier look and maintains the reliability and performance Rolex is known for. I often hear Eric Wind tell collectors the following when considering their first Rolex: “Vintage Datejusts are grotesquely undervalued. They are almost half the price of a brand new Rolex Datejust. They can be made water resistant quite easily. You can’t go wrong with a great vintage Datejust. It is just a perfect choice and looks great on everyone.” When considering size, the 1990s have a bit more heft and sportier feel and are also more practical with the quickset movements. Once again, the variety of dials make it one of the most compelling watches to pursue.

Eric has really taken a strong interest in keeping a variety of Datejusts in the office, as many clients become deeply connected to them and they offer tremendous value. As he wrote earlier this year in his article Don't Sleep On This: The Simple Vintage Rolex Datejust In Steel:

“As time has gone by, my appreciation and love for the Rolex Datejust has grown significantly. I’m constantly amazed by the quality and differentiations of the dials that Rolex used in vintage Datejusts over the decades. I have found the Rolex Datejust to be one of the most versatile watches a person can have. Whether you’re opting for the reference 1601 with a steel case and fluted white-gold bezel or the reference 1603 with the engine-turned steel bezel, they are watches which can be worn at the beach or pool, or even selectively with a tuxedo. The Rolex Datejust is certainly worthy of being in the running as the perfect one-watch collection.

The Datejust is special both because of its innovation being one of the first automatic watches with a date complication, but also due to the fact Rolex has always committed to offering the Datejust as one of the pillars of their company. Their pride in this watch is evident in the fact that every Datejust ever sold has been a certified chronometer, whereas many Submariners (such as the reference 5513) were not chronometer certified.”

7) Rolex Explorer Reference 1016

The Rolex Explorer reference 1016 is the epitome of simplicity and timeless. It is one of the most sought after models from collectors. This iconic watch was produced from circa 1960 until 1989. Over the course of the production very little was changed aesthetically. Collectors love how these dials change over time. Whether it be a tropical dial, the gilt font matching beautifully with the lume, or the nuances in coronets and font. It it is highly legible. The cases are very casual, but also capable for any rugged scenario. It is very frequent that I hear collectors state the reference 1016 as being the most frequently worn watch within their collection.

8) Rolex Explorer II Reference 1655

The Explorer II is somewhat of a ludicrously niche watch - a watch Rolex designed for speleologists or scientists who study caves. The oversized orange 24-hour hand is clearly the focus for the watch rather than the hour and minute hands and given how niche they were and how beat-up many of the surviving examples, “finding a good example is almost as tough as finding a great Paul Newman” according to Eric Wind. Many of these watches have over polished cases and others have white “albino” lume with a pale 24-hour hand not nearly as nice as the vivid orange variants. Just please don’t settle for a junky example!

9) Rolex Zenith Daytona Reference 16520 and 16528

While many are attached to the concept of in-house movements, one of the best examples where collectors embrace the opposite is the “Zenith Daytona”. The Zenith El Primero is regarded as one of the most exceptional automatic chronograph movements ever produced. Rolex began using the Zenith El Primero movements in their first automatic Daytonas starting in 1988. In 2000, Rolex would transition to their in-house chronograph calibre 4130. Over recent years, these “Zenith Daytonas” have appreciated significantly as collectors respect the modified Zenith El Primero movements by Rolex and the symmetry of the dials. These models represent a departure from the earlier manual-wind Daytonas and are seen as a significant evolution within the Daytona family. Along with the benefit of a perpetual movement, collectors often cite favoritism for these models due to the size, durability and wearability compared to the manual-wind models pre-1988.

10) The Paul Newman Daytona

Talking with Eric Wind and working at Wind Vintage has given me a deep appreciation for Paul Newman Daytonas. As Eric said, “There is nothing like a great Paul Newman. The dials are so unusual they almost look like they have been transported from another world. They are obviously not the most sophisticated or complicated watches in the world, but the dials are just outstanding and Paul Newman Daytonas have transcended the world of watches to become iconic objects - something you just want to own if you have the means to own one, regardless of whether you are a watch collector or not. You can make the case that they are overvalued, but I think a great example with provenance is probably undervalued today if you compare supply to demand.”

If you are interested in finding an exceptional vintage Rolex for your personal collection, please reach out to info@windvintage.com!