The best Rolex watches to invest in, according to Rolex experts

Watch prices have fallen since a 2022 high, meaning now might be the time to bag that Rolex you've been dreaming of
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Rolex is nicknamed The Crown for a reason: it is the king and queen of horology, and probably always will be. This makes Rolexes the ultimate investment watch, because thanks to iconic designsm high-quality craftsmanship and locked in cultural cache, they are still relevant and as desirable as ever.

“Rolex has always been one of the most coveted brands in the world, simply because they don’t try to be something they are not,” says Dillon Bhatt, watch and lifestyle expert and founder of LuxForte. “They do the basics phenomenally well, and then there’s a whole world of rare handicrafts that the general population might not even know about — with their off catalogue pieces, gem-set watches and rare dials. There is truly something for everyone at every price point, whether it’s your first watch or your hundredth.”

That said, high desirability combined with a tight supply makes some models difficult to get – which means they hold their value better than others over time. So if you’re trying to get your hands on one, which is the best Rolex to invest in?

A selection of Rolex Stella Day Dates, with thanks to Christies, Rolex Passion Market, Momentum-Dubai, Phillips, Sotheby's and The Watch Collector.

“The one that catches your eye first, that makes your heart beat a little bit faster,” says Bhatt. “The last three years in the watch industry have taught us that whatever goes up rapidly, will come down rapidly. Buying a watch should be about wanting to wear it, not keeping it in a safe hoping the value will somehow outperform stock markets.”

According to Bhatt, vintage Rolex is making a strong comeback. “Stella Day Dates have always performed well in auctions,” he said, referring to the bright, candy-coloured Stella enamelled dials that came about in the '70s (and are presumably named after the now-defunct Swiss company that provided the lacquer). Justin Bieber owns the playful model with a money-green dial, and Victoria Beckham has been seen sporting a yellow-gold Datejust with an aqua-green Stella dial. Also, let’s not forget that people – Kendrick Lamar included – lost their minds over the Oyster Perpetual models with Smarties-coloured dials in 2020. Although discontinued now, they were a major wink to their ancestors.

Rolex King Midas

For Brendan Cunningham, Professor of Economics, Eastern Connecticut State University and author of a book on Rolex, vintage is also the way to go when deciding the best Rolex to invest in. “I would recommend the asymmetrically cased Rolex King Midas. In many ways, it is the most versatile option for a collectible Rolex,” he says. On a leather strap, with moderate condition issues, this design can be found for mid-to-upper four figures (US dollars), while the most pristine examples, with precious metal bracelets, are priced closer to $50,000. “I still believe there is a lot of upside in these watches, though. Rolex is currently renewing its selection of dress watches and the King Midas is an important part of the brand's dress watch legacy.”

As Cunningham points out, quirky dress watches are having a moment and the King Midas (a fave of Abel Tesfaye, aka The Weeknd) is solidly in that category. “If rumours of a Rolex museum hold true, we're likely to learn more about the origin of the Midas, which will renew interest in the design,” he adds.

Kenichi Abe, of the popular watch shop Jack Road in Tokyo, echoes this sentiment. “When it comes to building a collection, vintage is better, especially from the '70s,” he says. “But they’re quite difficult to get recently.”

Sotheby's

Abe is all about the Daytona, one of the holy grails of collecting. “It was made for motorsports to calculate the speed, and became iconic because of Paul Newman,” says Abe. John Mayer, Chris Pratt and Ed Sheeran are fans of the Daytona (and the ‘Bad Habits’ singer does have some good habits, wearing his on a leather strap, just like the Newman did).

Abe also mentions the GMT-Master II, a model made originally for Pan-Am pilots. Abe says like David Beckham, he would go for the brown dial for both models (“I like brown”, says Abe.) A casual version with a black and grey bezel was released this year at Watches & Wonders.

But before reaching for your credit card, Abe advises: “The most important thing is to maintain it. For a vintage piece, get it serviced every three to five years. This way, it will last for a very long time.”