It’s one of life’s rich ironies that it’s probably easier to buy a treasured vintage Rolex watch these days than it is to buy a brand-new one.

The one thing to bear in mind when contemplating which vintage Rolexes to collect is that to some extent Rolex is a victim of its own incredible success. As it is one of only a handful of brands that continue to appreciate in value, there are many copies out there. And in some cases, you may be holding a genuine vintage Rolex case in your hands but someone has swapped the original movement or parts, rendering your watch a ‘Frankenstein’ as they are known, knocking a big chunk off the value in the process.

Whether you’re looking to buy an entry-level piece to get your vintage Rolex collection started or you’re ready to spend a bit more (all right, a whole lot more) for a model that you truly adore, we’ve scoured our curated vintage Rolex collection at Vintage Gold Watches to bring you a range of Rolexes at different price points. These pieces are sure to grab your attention and make a commanding presence on your wrist.

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 that has some unusual and much sought-after features that collectors fight for. This keeps its value climbing as the years pass.

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

It’s another irony that collectors often crave the lack of some of the elements 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 it as the Submariner 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. It’s 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. A subtle, but important difference, 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 containing less radium.

A further rarity, 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. 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 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 easily readable 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, for instance, the red “10,” indicating 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 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, which contributes to their rarity. In some cases, the damage sustained by the cases may render them irreparable and unable to be restored.

Its exquisite art-deco design lends itself to a more formal or dress watch, despite gaining considerable popularity for its practical features. With its historical significance in Rolexes 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 watch was specifically crafted to pay tribute to the brave accomplishments of the Royal Air Force pilots during the Second World War. Why would a German-born watchmaker in Switzerland pay tribute to the Royal Air Force? Hans Wilsdorf founded Rolex in London in 1905, and it was atop a horse-drawn omnibus while commuting to his office in Haymarket that he conceived the name Rolex. His links to Britain remained strong, so much so that, he saw fit to pay respect through the Air-King.

Rolexes 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 in the Air-King; it uses the Milgauss 3131 movement. This is because the Air-King was originally made for pilots travelling long distances, and precision timekeeping was critical. Rolexes patented blue Parachrom hairspring offers enhanced resistance to magnetic fields and provides excellent accuracy and reliability.

The Air-King model in our collection 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 a Oyster Perpetual Air-King is one of the best vintage Rolex watches to add to any collection.

Rolex Datejust Turn-O-Graph Ref 1625

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 Ref. 6202, released 70 years ago in 1953, was Rolex’s first sports watch but that first was outshone by the revolutionary design of the graduated, rotating bezel.

The Turn-O-Graph 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.

Looking at the earliest examples, it’s clear Rolex’s Turn-O-Graph was the testing ground for the Rolex Submariner. Both of them looked remarkably similar. The Submariner went on to become Rolex’s most popular sports watch, however, it’s the Turn-O-Graph which broke new ground.

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 invention of the cyclops date window is a fascinating story. By chance, Rolex founder Hans Wilsdorf splashed a drop of water on his watch and immediately noticed how it magnified the date. He quickly ushered in the cyclops – reminiscent of a drop of water – as an easy way to read the date.

The Ref. 6202 looks very similar to this Turn-O-Graph model ref.1625 that is currently for sale at Vintage Gold Watches. The Ref. 1625 was launched in 1958 and enjoyed continuous production until 1977. Model Ref. 1625 is a fantastic example of a scarce Datejust Turn-O-Graph in excellent condition. The example you see here 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 in the wild 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 forever remain strong.

Rolex Oyster Perpetual Day-Date Ref.1803

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’. It earned its moniker because it was worn and loved by royalty, presidents, dignitaries 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 the two most useful functions of a watch. In his pursuit of excellence, he finally designed a waterproof, self-winding wristwatch with a jump calendar system. The Day-Date was an instant hit amongst the well-heeled. Updated movements and dial variations followed over the years, and 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 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 Ref.6105 18ct 1952 Red Date

Introduced in 1945, the Rolex Datejust revolutionised the watch industry as the world’s first self-winding wristwatch with a date feature. Its exceptional waterproof capabilities, along with its remarkable accuracy and reliability, earned it widespread acclaim during that time.

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). It also distinguished itself by featuring a central seconds hand, unlike the more common subsidiary seconds dial. 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. As Michael Caine might say, not a lot of people know this but the “just” in Datejust signifies “just in time,” highlighting the watch’s ability to instantaneously advance the date at midnight without any delay.

The 1950s were the halcyon days of elegant men’s dresses watches in general and Rolex dials in particular. 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.

This watch was crafted from 18ct solid gold, as were all such models during the initial seven years of this model’s production. It bears the distinguished Rolex model reference 6105 and is 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.

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These six fine 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, we are committed to excellence and helping people find the perfect vintage watch that reflects their style and personality. Don’t worry if the particular model you want is sold, just talk to us and we will be happy to source another fine piece for you.

Call us on 020 7727 7095 to make an appointment or shop our vintage watches and accessories on our website.

Alan Wood
Alan Wood, founder of Vintage Gold Watches, is a trusted vintage watch dealer with 35+ years of experience. His passion and expertise have earned him a respected reputation in the industry. Vintage Gold Watches, established in 2011, is known for Alan's knowledge and skilled restoration team. With a love for vintage watches since his youth, Alan is thrilled to share the finest timepieces from the 1950s, 60s, and 70s with others, fueling his obsession.