The Best Vintage Rolex Watches to Collect 

The Best Vintage Rolex Watches to Collect 

By Alan Wood

Discover 6 of the most collectable vintage Rolex watches to add to your collection. As curated by Alan Wood at Vintage Gold Watches.

Alan Wood (above) is a trusted vintage watch dealer with over 35 years of private collecting experience. After founding Vintage Gold Watches in 2011, his deep knowledge and infectious passion for mechanical timepieces earned him a highly respected reputation in the industry. Vintage Gold Watches has become a renowned dealer thanks to Alan’s expertise and skilled team of restorers. Alan’s love for vintage watches started as a young Mechanical Entrepreneur and grew into an obsession. He believes the finest watches were made in the 1950s, 60s, and 70s, and is thrilled to share them with others.

The Best Vintage Rolex Watches to Collect

Whether you’re interested in buying your first vintage Rolex watch for everyday wear or looking to start a vintage watch collection, this guide takes you on a journey through Rolex’s most collectable vintage watches. 

We’ve collated a range of vintage Rolex models that we believe are both collectable and  likely to gain value in years to come.

Rolex Submariner

While perhaps not the model with which to start your vintage Rolex collection, the Submariner Ref.5508 from 1957 is a fine example of a Rolex with some unusual and much sought-after features that collectors fight for. This model keeps climbing in value as the years pass.

The Rolex Submariner was officially released at Baselworld in 1954. Not even the most optimistic Rolex executive could have had any inkling of how popular and sought after it would become in the decades to follow. When it became linked to the British spy James Bond, its appeal became even greater.

Collector’s often seek models lacking some of the features that have made a modern-day Submariner all the more robust and damage-proof, such as a crown guard and a ceramic bezel. The 1950s Submariners have no crown guard, which defines them as the Submariner model worn by James Bond in the first four 007 films. As this model was made circa 1959, it is one of the last produced without the crown guard and the first Submariner model to feature the ‘square-shaped’ typeface on the bezel.

Even better, this Rolex Submariner 5508 features a calibre 1530 chronometer grade movement. Introduced in 1957, it’s in outstanding condition with original brass, not Teflon as in later models.

One of the most exciting elements of this watch is the extremely rare ‘Exclamation Dot’ dial. It is a subtle but important element whereby a small dot appears above the 6 and below the baton indices. This was Rolex code for a change in lume used on the watch that contains less radium. Contributing further to its value is the highly desirable sign of ageing in the ‘Ghost Bezel’ whereby the bezel has bleached over time from black to grey, rather like a beloved pair of Levi jeans.

This is a first-class original example of a rare 1959 Ref. 5508 with the much sought-after Exclamation Dot Dial and Ghost Bezel elements. This vintage Rolex Submariner makes an excellent investment and heirloom piece. Even though vintage Rolex prices have risen markedly of late, we believe excellent examples such as this remain undervalued.

Rolex Prince Jump Hour

The Art Deco-inspired Rolex Prince, though perhaps not as widely recognised as other Rolex models, holds immense significance in the brand’s heritage. It played a pivotal role in elevating Rolex to the upper echelons of luxury watch manufacturing nearly a century ago.

The original Rolex Prince watches were renowned for their exceptional timekeeping precision. Many Prince models featured two dials, making them particularly popular among doctors who could easily time a patient’s pulse using the easy-to-read seconds hand positioned at the bottom of the dial. Consequently, it earned the nickname “the doctors’ watch.”

The Rolex Prince Jump Hour was the world’s first true digital watch, featuring an aperture window at the top of the dial with an hour indicator wheel. By observing the Rolex Prince Jump Hour, one can notice the red “10” that indicates the time as 10:30 and 30 seconds. Production of the Prince Jump Hour ceased in the late 1940s when the Art-Deco style fell out of fashion, but it was revived in 2005.

This particular model, crafted from exceptionally rare 18-carat yellow and white gold, is the Chronometer version and remains in its original, unrestored, and untouched condition. The movement housed within this timepiece is of remarkable quality. Introduced by the founder of Rolex, Hans Wilsdorf, in December 1930, the Rolex Extra Prima is a 15-jewel hand-wound movement used only in Rolex’s highest-quality watches during that era. It represents an extraordinary example of a truly historic watch, solidifying its position among the more coveted vintage Rolex models to collect.

A note regarding rectangular cases: When acquiring a vintage rectangular or square watch, it is crucial to ensure that the case exhibits no signs of wear, fatigue cracks, or pinholes, particularly around the hinge and corners. These types of cases are prone to wear and tear in these areas, contributing to their rarity.

Despite gaining considerable popularity for its practical features, its exquisite Art-Deco design lends itself to a more formal or dress watch. With its historical significance in Rolex’s history and its unique design, the Rolex Prince definitely deserves a place in your vintage Rolex collection.

Rolex Oyster Perpetual Air-King

The Rolex Oyster Perpetual Air-King represents a perfect blend of aviation heritage, elegant design, and robust functionality. It’s a timepiece cherished by watch enthusiasts and collectors alike, and it continues to uphold Rolex’s reputation for creating exceptional watches. Introduced in 1945 as a member of Rolex’s Air series, the Rolex Air-King was specifically crafted to pay tribute to the brave accomplishments of the Royal Air Force pilots during the Second World War. 

Rolex’s Oyster Perpetual series is the longest-established model still in production in the brand’s history. It has been the cornerstone of their production since the 1930s. The Oyster Perpetual Air-King is a great entry-level vintage Rolex. The Air-King Oyster Perpetual has some differences from the classic Oyster Perpetual, the most obvious being the profiles of the case. The Air-King is about 2 millimetres bigger (at around 13.25mm) than the Oyster Perpetual. This is due to the Air-King having 2 cases, an inner case and an outer case.

The other notable difference is the movement. The Air-King uses the Milgauss 3131 movement. This is because the Air-King was originally made for pilots travelling long distances, and precision timekeeping was critical. Rolex’s patented blue Parachrom hairspring offers enhanced resistance to magnetic fields and provides excellent accuracy and reliability.

This Air-King model is a first-class example of a vintage Rolex Oyster Perpetual Air-King which is ready to wear and practical for everyday use. If treated with care, it will make an excellent investment or heirloom piece. As each year goes by and the world market for vintage gold Rolex watches continues to increase, prices, like the Air King itself, will continue to soar. This is why we believe an Oyster Perpetual Air-King is one of the best vintage Rolex watches to add to any collection.

Rolex Datejust Turn-O-Graph

The launch of the Rolex Turn-O-Graph was highly significant in the development of Rolex as a company and for watch-making innovation in general. The Turn-O-Graph Ref. 6202 was the first to be released in 1953, following the Datejust in 1945, around a year before the Submariner in late 1953/early 1954.

The Turn-O-Graph was Rolex’s first sports watch and features a stainless steel case, typically measuring 36mm in diameter, although there have been variations with larger case sizes over the years. It has a screw-down crown that ensures water resistance and protects the movement from moisture and dust.

One of the distinctive elements of the Turn-O-Graph is its rotating bezel with a graduated scale. The bezel can be turned in both directions and is typically marked with 60-minute graduations or hour markers, allowing the wearer to track time or measure elapsed intervals, similar to a chronograph, without the cost of a complicated chronograph calibre. This successful innovation was quickly adopted by many brands after Rolex’s introduction.

The model Ref. 6202 was replaced in 1954 by the much-revised model Ref: 6309 which effectively returned the Turn-O-Graph to the Datejust family as a date function. A cyclops window was added along with the new engine-turned bezel with markers every five and ten minutes and can be seen on Turn-O-Graphs ever since.

The Turn-O-Graph model ref.1625 was launched in 1958 and enjoyed continuous production until 1977. Ref. 1625 is a fantastic example of a scarce Datejust Turn-O-Graph in excellent condition. This example is an early, extremely rare and collectable, 18-carat pink gold Turn-O-Graph with the original Rolex 18-carat pink gold bracelet. So rare is it that we have never seen a pink gold Turn-O-Graph in its original pink gold bracelet before. 

The original, high-grade “Officially Certified Superlative Chronometer”, 26 Jewel, Calibre 1560 movement is highly regarded for being extremely accurate, reliable and strong. This was also the first movement to incorporate the instant date change at midnight. It’s rare enough to find a Pink Gold Turn-O-Graph as early as this one, but to find one complete with its original Pink Gold bracelet is practically unheard of. Vintage gold Rolex Datejust watches are highly collectable and the rarity of this watch means the value will remain forever strong.

Rolex Oyster Perpetual Day-Date

The Day-Date has become one of the most legendary watches of all time, and it’s a reputation that has been well earned. First released in 1956, it was dubbed ‘the President’ because it was worn and loved by royalty, presidents and numerous luminaries. It found its way onto the wrists of several US presidents including Lyndon Johnson and JF Kennedy. Known for their marketing astuteness, in 1966, Rolex emphasised this connection with the Oval Office in their advertising campaign for the model.

The last masterpiece of Rolex founder Hans Wilsdorf, the Day-Date is considered by many to be the pinnacle of his work. In Wilsdorf’s opinion, day and date were a watch’s two most useful functions. In his pursuit of excellence, he finally designed a waterproof, self-winding wristwatch with a jump calendar system. Updated movements and dial variations followed, and over the years the model became viewed as the Rolex.

With the Day-Date’s expanding popularity came the opportunity for greater personalisation, and a vast array of dial choices became available: anything from fine burlwood, precious stones like onyx, and the so-called ‘Stella’ dials with their bright colours all became available. The last frontier in ostentatious design came in the form of jewelled Day-Dates. From delicate diamond dial markers to fully iced-out cases. It may well have been this extravagant customisation that made Rolex so ubiquitous as a luxury brand that it has become almost its own kind of currency.

This specific example of a 1958 Day-Date Ref. 1803 in 18-carat gold is a fine illustration of a collectable Day-Date in museum condition. Set in the mid-price range category, it’s certainly an investment piece but not too far beyond the reach of most collectors’ dreams. With a Cal.1556, 26 Jewel chronometer movement and its original sunburst dial and 18-carat yellow gold case in immaculate condition, it hasn’t lost any of its charisma over the years.

Vintage gold Day-Date watches are highly collectable and the rarity of this watch means the value will always remain strong. The Day-Date provides an excellent financial investment as well as something to wear, treasure and enjoy. It is a highly practical vintage watch and makes for the perfect evening wear dress watch as well as an accurate and reliable timepiece to use on an everyday basis.

Rolex Oyster Perpetual Datejust

Introduced in 1945, the Rolex Datejust revolutionised the watch industry as the world’s first self-winding wristwatch with a date feature. The “just” in Datejust signifies “just in time,” highlighting the watch’s ability to instantaneously advance the date at midnight without any delay. Its exceptional waterproof capabilities and remarkable accuracy and reliability earned it widespread acclaim.

The Datejust made its debut in what was considered at the time a large size, measuring 36mm in diameter (excluding the Rolex screw-down crown). Unlike the more common subsidiary seconds dial, it also distinguished itself by featuring a central seconds hand. This timeless design swiftly became an emblem of style and excellence, retaining its production and development for over 70 years with minimal design alterations.

In 1956, Rolex introduced the Day-Date, which, alongside the Datejust, continues to hold the position of Rolex’s premier men’s line of dress watches. However, early Datejust models are rarer and highly sought after, commanding higher prices than the Day-Date. 

A masterpiece of timeless style, simplicity and elegance, this Ref.6105 18-carat 1952 model has a rare dial with ‘dagger’ and ‘spearhead’ hour indices that is difficult to find and quite sought after. Here in ivory cream, it contrasts beautifully with the yellow gold case. With the original ‘Lance’ hands and yellow centre seconds as well as the rare red date wheel, this watch is brimming with 1950s charm and elegance. 

It bears the distinguished Rolex model reference 6105 powered by the revered Rolex Chronometer grade Cal.A296 movement, adorned with 18 jewels. Such extraordinary quality and impeccable condition are a rarity among early Datejust watches, making this particular piece a true gem from the early production years and would be a shrewd addition to any vintage Rolex collection.

Keep up to date on vintage Rolex stock

These examples of the best vintage Rolex watches to collect should keep you fantasising about your dream vintage Rolex collection all day. To stay up to date on vintage watch news, sign up for our weekly newsletter and be the first to see our new stock before anyone else. 

If you are looking to buy a vintage Rolex, we are always happy to help at Vintage Gold Watches. Don’t worry if the particular model you want is sold, just talk to us and we will be happy to source the model you are looking for.

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