Imagine a billionaire on his yacht anchored off Capri – or Sentosa, for that matter. Rather than having inherited money, he is an entrepreneur. Dressed comfortably but expensively, our tycoon is earning millions an hour from his multinational ventures, while he chills on his latest acquisition.

And what is on his wrist? It’s likely to be something very large, probably a chronograph or a tourbillon, either in rose gold or diamond-like carbon-coated steel or titanium. Basically, it’s either big and bright, or big and very dark. And it may have a state-of-the-art ceramic inlay, carbon- fibre insert or rubber strap.

Even though the type of watch is easy to profile, the choice of brand is bewilderingly wide. That’s because the luxury sports watch makes up a huge and very valuable segment of the watch industry. But the watch itself is a relatively new phenomenon.

Fifty years ago, the luxury sports watch as we know it today didn’t exist. The Royal Oak hadn’t been invented and Hublot had yet to be established. In the 1960s, the Rolex Submariner was still a diver’s tool and reasonably affordable. Both Che Guevara and Fidel Castro wore Rolex watches when they were revolutionaries.

It was Audemars Piguet which fired the first shot in 1972, when it unveiled the Royal Oak. Created by Gerald Genta, who at his peak was the most influential timepiece designer in the business, the octagonal steel watch was more expensive than many gold watches of its time.

And then in 1980, Hublot came along with its distinctive rubber straps, the first time the material was used on a high-end timepiece. Both those watches turned inexpensive materials – steel and rubber – into coveted centrepieces.

Even so, it was slow going for the luxury sports watch, until the turn of the century, when everyone else tumbled into the market. New brands like Richard Mille set up shop and old brands like Panerai were revived, solely to cater to the market for luxury sports watches. Throughout all of this, Rolex rolled along, making what was essentially the same watch incrementally better and incrementally more expensive, taking it off the wrists of jungle-bound revolutionaries and onto those in boardrooms.

But this cycle is coming to a close. Even though the yacht-borne tycoon is still likely to sport an enormous rose-gold watch, a small number of the well-heeled is going in the opposite direction.

Instead of the new and shiny, they are seeking out the old and worn.

They are seeking out vintage Rolex sports watches, which are mostly robust enough to be worn near water. These are slowly turning into the status symbols of the moneyed, discerning and sophisticated.

At posh cocktail parties where the talk revolves around art with eight-figure price tags, or at fine-dining restaurants on the Michelin Guide radar, there will likely be someone with a vintage Rolex on his, or her, wrist.

This has pushed the prices of vintage Rolex watches through the roof – think five to six figures. And, though the trend started with the type of people who read high-brow magazines, it is spreading to more mainstream collectors.

The reason: Watches, especially luxury sports watches, are status symbols. But timepieces that are status symbols have become relatively common. Walk onto Nikki Beach in St Tropez, and the oversized watch in rose gold will be in abundance.

Though still uncommon, the vintage Rolex is recognisable enough to be a possession of prestige. Arguably the most coveted model, the Daytona “Paul Newman” is distinctive enough to be spotted from a distance. It is discreet, but not overly so.

Alongside this rise in the demand for such timepieces has been the emergence of a globetrotting group of vintage-watch dealers. And so it has all come full circle. The Rolex once worn by communist revolutionaries is now a status symbol of the cognoscenti. Precious, no?