Investing in a classic is an investment that keeps on giving. Interest in alternative investments such as classic cars, art and watches has increased dramatically over the past few years. It is not only about hedging your bets 
and an appreciation for finely crafted, mechanical objects, but also about a more meaningful engagement with an investment that increases in value over time and brings great joy while doing so.

For example, my 1972 Jensen Interceptor S3 has more than trebled in value since I acquired her a few years ago, and anyone who bought a Rolex 
Submariner 10 years back will know that at the very least it has retained its value – depending on the model, of course. 

While eyeing the new platinum Oyster Perpetual Day-Date 40 with its ice blue dial and new mechanical movement, Calibre 3255, I spoke to Cape Town-based vintage Rolex dealer Pieter Bester for his advice on the most desirable models from the past. 

Bester may prefer the “more collectable sports watches”, but the modern update of the Day-Date in its 40mm case sets a new standard for both accuracy and elegance. The first Day-Date made its debut in 1956 and according to Rolex has been “worn by more presidents, leaders and visionaries than any other watch”. It was the first waterproof and self-winding chronometer wristwatch to offer a modern calendar with full day display.

Rolex made its first watches in the early 1900s, with the revolutionary Oyster waterproof case first appearing in 1926. But it was the sports pieces launched from 1953 onwards that were the real turning point for the company. Rolex began making its pioneering “tool watches” in a time when deep-sea diving, aviation, mountain climbing and exploration still had sex appeal and were the professions of truly hardened adventurers – the “watches of achievers”. 

“These iconic tool watches helped shape our understanding of Mother Earth. It was conceived with professionals in mind, and to that end it served a noble purpose,” says Bester.

It is from this period that the collectable pieces start appearing — the Submariner, GMT-Master, Sea-Dweller, Cosmograph, Explorer and Milgauss, establishing a lasting following based on their incredible innovation and associations with the great explorers and racing drivers. 

According to Bester, the sports pieces are more collectable and the prices are subject to supply and demand based on rarity and desirability. For example, “more people collect Submariners, but no collection is complete without one of each of the sports models. Stainless steel models are the most desirable, followed by two-tone and gold.”

With classic cars there are different schools of thought on how "original" a model needs to be to retain its collectible value — some prefer to strip and restore cars to their original factory condition while others prefer a more authentic, aged patina. When it comes to watches, the latter is more important. The main criteria is doing your homework or having someone like Bester to advise you before you drop a briefcase full of cash. 

“I saw a beautiful GMT-Master for sale recently, but upon closer inspection I noticed its original Tritium dial and hands were re-lumed during a service. This ‘loss’ of original patina makes it less desirable and certainly halves its collector value.”

Collectability spikes when the original box and papers “the birth certificate” is present. “Sure, an original box can be bought on, but the original 
papers cannot be replicated and are therefor more important, driving the price up even further.” 

Early Submariners can fetch astronomical prices at auction, according to Bester. Steve McQueen's 5512 recently sold for $234,000. Granted, it was also due to his association, but nevertheless sought-after vintage Submariners are always a good investment. That’s impressive considering the new Submariner currently retails for about R100,000. 

“A very rare Paul Newman Daytona recently sold for just over $1m. Current models, however, are produced in larger numbers than ever before, so the rarity factor is slightly different." 

Bester’s prized possession is his birth year 1972 Rolex Submariner 5513 with its beautiful serif dial and “incredible patina”.

“The Holy Grail for many a collector would be acquiring the so-called ‘James Bond’ Submariner without crown guards, or a military issue Submariner, fondly referred to as a ‘MilSub’. So special.”

When it comes to vintage wristwatches, “you are buying the seller, not the item”, he says. “Trust is still key. I will take back any wristwatch I sell because I know its history and I certify it ‘clean’. No stolen watches here, thank you very much.” 

If you are in the market for a classic piece and have around R50,000 to spend? 

“Vintage Rolexes are becoming more and more difficult to find at that price point, but there are examples of beautiful DateJusts available. These were, and still are, the mainstay of Rolex's sales worldwide.”

Back to the Day-Date, time is ticking on and in this case at twice the accuracy 
of an official chronometer. The new-generation calibre is impressive with its power reserve extending to 70 hours – and, like the Milgauss, it is impervious to magnetic interference, should you have to concern yourself with such things.

I appreciate attention to detail, fine craftsmanship and technological 
advancements, though man’s obsession with time could be better spent taking time off. At least with the calibre 3255’s impressive power reserve you can take your Rolex off on Friday evening and only look at it again on Monday morning – if you can go without it for so long, that is. 


Rolex Oyster Perpetual Day-Date 40 (Reference number: 228206)
40mm platinum case on President semi-circular 3-piece bracelet 
Calibre 3255 movement
Ice blue diagonal motif dial

Image: Supplied

Rolex Oyster Perpetual Submariner Date (Reference number: 116610LV)
40mm 904L stainless steel case on Oyster flat 3-piece link bracelet
Calibre 3135 movement
Green dial with bezel is unidirectional rotatable 60-minute graduated, with scratch-resistant Cerachrom insert in ceramic

Image: Supplied

Rolex Oyster Perpetual Milgauss (Reference number: 116400GV)
40mm 904L stainless steel case on Oyster flat 3-piece link bracelet
Calibre 3131 movement with perpetual, mechanical, self-winding, with a magnetic shield
Z-Blue dial

Image: Supplied

For more information visit or 
email Pieter Bester

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