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Feature: The Rolexes you can wear with ANYTHING

Thinking of buying a Rolex but concerned that it might not quite fit in with your everyday outfit? Not every model in the Crown’s catalogue is versatile enough to be worn anywhere, but these three stalwarts of the brand definitely pass the test.

Rolex Oyster Perpetual 39mm

Forget the Daytona and the Submariner, the Oyster series is the foundation on which Rolex built its iconic status. Often referred to as an “entry-level” model, it remains for some the quintessential all-steel, no-frills Rolex. That the design has barely changed in decades is testament to its perennial stylishness. It’s a watch you can wear with a poncho or your pyjamas.

Rolex Datejust

The Datejust is Rolex’s bestselling model thanks to its versatility and range of designs and colours. For a look suitable for any occasion, we think a pared-down steel and white gold number with classic baton hour markers or Roman numerals would make an ideal daily beater and be smart enough for those all-important business trips.

Rolex Submariner

Although a dive watch at heart, the classic black-bezel Submariner’s understated design makes it the perfect watch for everyday wear. Pair it with your favourite suit to channel your inner James Bond, or take it along on a beach holiday where, rest assured, this iconic and robust Rolex will faithfully keep ticking if you decide to go for dip.

Plus, three that you can’t…

Rolex Deepsea Challenge

It would be easier to push a rhino through a rubber ring than get this behemoth to slip under your shirt cuff. At a whopping 50mm, the Deepsea Challenge is not so much a watch as a hockey puck on a bracelet and as such should never be worn with a suit. Frankly, the only time this should be seen in an office is when it’s being used as a paperweight. This one is strictly for the beach—or actual deep-sea diving.

Rolex Cellini 50519

Rolex’s dressiest collection, the Cellini, was inspired by Renaissance-era sculptor and goldsmith, Benvenuto Cellini, and was discontinued in 2023, replaced by the 1908 line. Coming in an array of precious metals, you might feel too flashy rocking this 2014 version to the office or neighbour’s barbecue party. Instead, we think it’s better reserved for those glitzy occasions where you dress your impeccable best.

Rolex Day-Date

A top-tier model commonly worn by CEOs, presidents and billionaires, this is a watch that commands respect. The Day-Date only comes in precious metals, with the exception of six ultra-rare steel pieces made back in the 1960s, and therefore shouldn’t suffer the ignominy of being worn with flip-flops and a vest. If you’re going to wear a Day-Date, think of the esteemed company you’re in—from the Dalai Lama to Warren Buffet—and dress accordingly.

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