The 10 Best Vintage Rolex Watches for Collectors

Jul 28, 2022

Category: Style

Regardless of what metric you go by, there is no more significant luxury watch brand on Earth than Rolex. From name recognition to reputation to actual sales numbers (Rolex accounts for nearly a third of today’s Swiss luxury watch market share), The Crown always comes out on top. So for anyone seriously considering a luxury watch, be they a seasoned enthusiast or a curious novice, Rolex is definitely going to draw some consideration at some point in their search. And for many looking into buying a Rolex watch, the question may eventually come down to whether they should purchase a modern Rolex or a vintage one.

Modern Rolexes are undoubtedly impressive. Increasingly positioned as serious luxury items, much of the brand’s current output is flashy and bordering on ostentatious. They’re still excellent watches and as durable as ever, but one could argue that they lack the charm of Rolex’s vintage pieces. Once upon a time, Rolex produced tool watches for the everyman. And while they were always positioned as a higher-end brand, they were still something most middle-class people could save up for fairly easily — something that can’t really be said about Rolex today. So to celebrate Rolex’s twentieth-century heyday, we’ve gone and compiled this guide to the ten best vintage Rolexes out there.

Why Vintage Rolex?

A Simpler Time

Rolex has been around since 1908, and the brand has been resoundingly successful for most of its history. From its early beginnings as a British-founded upstart disrupter to its current standing as the Swiss luxury watch standard, Rolex has always left a big mark on the watch industry. But for our money, the period when Rolex shined brightest was from the 1950s to the 1980s. It was during this time that the brand was at its most imaginative and groundbreaking, as Rolex pioneered waterproof cases and pushed them to their limits, while also inventing useful everyday complications like the GMT.

This era also saw Rolex debut many of its best-known models, including the Submariner, Daytona, GMT-Master, and Explorer. All of these watches were purpose-built tools designed for divers, drivers, pilots, and adventurers, and their simple styling became associated with mid-century cool. It’s this combination of romanticized use by men of action and timeless, rugged aesthetics that have led to the market for vintage Rolexes being arguably the hottest in the entire watch industry. And with that popularity comes high prices — very high, in some cases. All of the watches in this guide will set you back at least five figures, with some routinely commanding six- and even seven-figure sums. It’s a bit ironic that Rolex’s more utilitarian timepieces often cost a great deal more today than the brand’s current ultra-luxury offerings, but prices are driven by the market and the market loves vintage Rolex.

Buyer Beware

The Pitfalls Of Vintage Watch Buying

Before we get into our list of the best vintage Rolex watches, it’s important to offer up a bit of a warning about buying vintage watches. As we mentioned already, these watches are all very expensive, and before spending this kind of money on anything — especially a decades-old mechanical device — you need to do your due diligence to avoid being ripped off. There’s a saying in the watch community that you “buy the seller” and not the watch, and it really rings true here. Make sure you look into who’s selling the watch and only purchase from a trusted dealer. The vintage watch market is a minefield full of scams, fakes, and cobbled-together “Frankenwatches,” and if you’re not careful you can easily lose thousands of dollars, so you should also heavily research the model you’re after so you know what inconsistencies to look out for. Finally, if possible, it’s also a good idea to consult experts on online forums and elsewhere to get a second opinion before making a purchase on any high-priced vintage watch.

Photo: Philly Time Co.

Rolex Cosmograph Daytona “Paul Newman”

Even if you’re not familiar with vintage Rolexes, you’ve probably heard of the “Paul Newman” Daytona. An example of one of these watches, owned by the eponymous actor himself, once held the record for the most expensive watch ever sold at auction after a buyer paid for $17.8 million for it in 2017. The Daytona is Rolex’s chronograph, and the only thing separating a “Newman” from a regular Daytona of the same vintage is the dial. “Newman” Daytonas have what Rolex used to refer to as “Exotic” dials. These dials, always in panda or reverse panda colorways, have a different font and slightly different markings compared to the standard Daytona dials, with their Art Deco numerals and square markings on the subdials being the most significant things to look out for. The dials were manufactured by a company called Singer, and they appear on a number of different Daytona references produced in the 1960s and ‘70s, but at a much lower rate than standard Daytona dials. Newman himself wore a ref. 6239, which has a steel bezel. More desirable is the ref. 6241, which added a black acrylic bezel. The most sought-after on the general market is the ref. 6263, which also has a black bezel but boasts a cleaner-looking dial. Daytona references 6262, 6264, and 6265 also came with exotic Paul Newman dials. Expect a six-figure price tag for basically any Paul Newman Daytona.

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Photo: eBay

Rolex Explorer Ref. 1016

In some ways, the Explorer is Rolex’s most basic watch. A simple three-hander that tells the time and nothing else, the utilitarian timepiece became a legend thanks to its association with Sir Edmund Hillary and Tenzing Norgay’s summit of Mount Everest in 1953. Rolex marketed the Explorer as accompanying Hillary to the top of the mountain, which wasn’t entirely true. The explorer actually wore a Smiths watch, while he kept the prototype given to him by Rolex — not yet called an Explorer — in his belongings, and it’s unclear if it actually made it to the summit. The Explorer officially debuted later in 1953 with the references 6150 and 6350 being the first to say “Explorer” on the dial, but 1960 is when the model really came into its own. That’s when the ref. 1016 debuted, by far the most popular Explorer model. Produced for nearly 30 years, there are loads of variations among 1016s in terms of dials and, to a lesser degree, movements, but any one of them makes an excellent addition to a collection. Plus, with prices starting in the low-five figures, they’re one of the best buys among vintage Rolex watches.

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Photo: eBay

Rolex Explorer II Ref. 1655 “Steve McQueen”

Debuting in 1971 as the concurrently produced sequel to the Explorer, the larger Explorer II quickly found a fanbase of its own. Sporting a fixed 24-hour bezel, lume at all 24 hour spots on the dial, and a bright orange GMT hand, the watch was designed for cave explorers and others who worked in darkness and needed their watch to distinguish day from night. The original reference of the Explorer II was the 1655, which lasted in Rolex’s rotation until it was replaced by the far more modern-looking ref. 16570 in 1985. Relatively unpopular during its production, the 1655 is now a hot collector’s item, though one has to wonder how much of that is owed to its “Steve McQueen” nickname serving as a stand-in for a much more expensive Rolex “Paul Newman.” However, unlike the late actor’s pal Newman and his Daytona, McQueen is not believed to have ever actually worn an Explorer II (though he did own a Submariner). But at this point, the nickname is firmly established and doesn’t appear to be going anywhere.

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Photo: Wind Vintage

Rolex GMT-Master Ref. 6542 “Pussy Galore”

At the dawn of international commercial travel in the early 1950s, Pan Am put out a call to Swiss watchmakers in search of something for their pilots to wear that could simultaneously tell the time in two places at once. The first to come up with something was Glycine with its Airman, which used a 24-hour dial in conjunction with a 24-hour rotating bezel. Not long after in 1955, Rolex launched the GMT-Master, which created the GMT complication as we know it today. The first iteration of the watch was the ref. 6542, which originally had a blue and red “Pepsi” bezel made of bakelite with luminous material underneath. This early plastic material was prone to cracking, and when an owner sued Rolex claiming that radioactivity from the lume in his 6542’s cracked bezel gave him cancer, the brand recalled the bakelite bezels and replaced them with non-luminous aluminum inserts. This action, coupled with the fact that the 6542 was only produced until 1959, has left very few bakelite examples left — and they routinely go for over $100,000 on the market. Those that are out there are frequently referred to as “Pussy Galore” GMTs, due to Honor Blackman’s ludicrously-named pilot having worn one on screen in the 1964 James Bond classic Goldfinger.

Purchase: Here

Photo: eBay

Rolex GMT-Master Ref. 1675

The successor to the 6542, the second GMT-Master skipped the drama of bakelite and debuted with a Pepsi bezel insert made from aluminum, along with crown guards, which the 6542 lacked. One of Rolex’s longest-running and most-beloved references, the 1675 was in production from 1959 until 1980, and it saw loads of innovation during that time period. From the all-gold, brown-bezeled “Concorde” to the two-tone “Root Beer” (also known as the Clint Eastwood, after… eh, you get how this works by now), there really is a 1675 out there for everyone. Two of the most desired variants among collectors are the early gilt-dial examples that feature gold printing on a glossy dial, and the later radial dials boasting a unique aesthetic with their indices pushed further toward the center of the dial. Those will both fetch a premium, but low five-figure prices are common for many of the more pedestrian 1675 examples, with the least popular examples (i.e. not Pepsi) sometimes even dipping into four-figure territory.

Purchase: Here

Photo: eBay

Rolex GMT-Master II Ref. 16760 “Fat Lady”

In 1982, Rolex introduced the GMT-Master II. Oddly enough, this did not immediately spell doom for the GMT-Master, as that watch remained in production as a cheaper alternative until 1999. The difference between the sequel and the original GMT was the GMT-Master II’s Caliber 3085 movement that allowed for independent operation of the local hour hand, a feature some refer to today as a “true” or “traveler’s” GMT movement. The new movement called for a thicker case, resulting in this watch’s nickname of the “Fat Lady” or, more flatteringly, the “Sofia Loren.” Produced until 1988, the ref. 16760 was the original GMT-Master II, and it switched things up in the watch cola wars by going from the blue-and-red Pepsi bezel of the 1675 to a black-and-red “Coke” insert. Prices are generally a tad higher than what you’ll see for an average 1675, but will lag behind more sought-after versions of its predecessor.

Purchase: Here

Photo: Philly Time Co.

Rolex Sea-Dweller Ref. 1665 “Double Red”

As perhaps the most famous watch in the world, the Submariner is unsurprisingly Rolex’s flagship dive watch. But it isn’t its only dive watch. Nor is it the brand’s best dive watch, at least from a diving perspective. That honor goes to the Sea-Dweller. Introduced in 1967 as arguably the first watch with a helium release valve, the Sea-Dweller was suitable for saturation dives as it allowed pressurized helium atoms to escape the watch without popping off the crystal — something that plagued divers lacking the feature. For good measure, the Sea-Dweller also greatly improved the Submariner’s water resistance, from 200m to 610m. The ref. 1665 was the first iteration of the Sea-Dweller, and it stuck around for 10 years. Nicknamed the “Double Red” due to its two lines of red text on the dial, the 1665 also introduced a date window to Rolex’s dive watches around the same time as the first Submariner Date, the short-lived ref. 1680, but it did so without the oft-maligned cyclops. Double Reds are pricey, generally starting in the neighborhood of $40-$50K.

Purchase: Here

Photo: Philly Time Co.

Rolex Submariner Ref. 6538 “James Bond”

You knew this was coming: we’ve finally made it to the Submariner section of this guide. As Rolex’s signature watch, the Sub’s vintage references are unsurprisingly popular with collectors, but some draw considerably more interest than others. Perhaps the most legendary, and the watch most responsible for Rolex’s reputation as a “cool” brand, is the ref. 6538. This is the watch that appeared on the wrist of James Bond during the character’s big screen debut in 1962’s Dr. No, and it’s represented suave sophistication ever since. Looking decidedly more mid-century than later Subs, the 6538 is beloved for its 8mm “big” crown, its (sometimes) hashmark-free bezel with a red triangle at 12, and its gilt chapter ring. Produced only from 1956 to 1959 and undoubtedly one of the coolest watches ever made, today the 6538 is also one of the most expensive. Expect to pay well above $100,000.

Purchase: Here

Photo: eBay

Rolex Submariner Ref. 5512

For a Submariner that’s considerably more affordable — and far more similar in appearance to Rolex’s modern divers — have a look at the 5512. Introduced in 1959, this is the watch that established the Sub’s iconic look that has remained largely unchanged for over 60 years. From the crown guards to the hashmarked bezel to the 40mm case size, this is immediately recognizable as a Submariner, and as a result, it’s the one on many vintage Rolex shoppers’ want lists. But which 5512 to get? Like a few of the other references we’ve mentioned, the 5512 was in production for a long time, from 1959 all the way to 1980. As a result, there are a ton of variations within its ranks, from square crown guards to pointed crown guards and gilt dials to matte dials. Serious collectors will obsess over these details, but if you simply want a vintage Sub, you can find a 5512 in good condition for around $25,000. A way to save a decent amount of money would be to go for the 5513 instead. Introduced in 1962 and boasting an even longer lifespan of 27 years, the 5513 was essentially a non-chronometer version of the 5512, and can be had for around ten grand.

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Photo: Menta Watches

Rolex Submariner Ref. 5513/5517 “MilSub”

Finally, we’ve come to this, the ultimate grail Submariner. The “MilSub,” as you may have deduced, stands for Military Submariner, and these stunners were never sold to the public — they were government-issued to the British armed forces. Rolex produced only around 1,200 total units across three references — 5515, 5513/5517, and 5517 — in the early 1970s, and fully-intact MilSubs are extraordinarily rare today, as many were modified after being sold by their original owners. True MilSubs have a number of distinguishing characteristics, namely sword hands, a unique bezel with markings for all 60 minutes, a circled “T” on the dial below the hand stack indicating tritium lume, and fixed bars between the lugs (i.e., these watches can only be worn on a one-piece or NATO strap). Thanks to their extreme rarity, military heritage, and objectively attractive looks, excellent MilSub examples can see prices climb to a quarter-million dollars or so.

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The Complete Guide to Every Rolex Watch on the Market

More interested in Rolex’s modern output? Then check out our comprehensive guide to every model currently offered by the Swiss luxury watch leader.

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