12 Best Rolex Watches for Men in 2023

Watchmaking's most famous brand earned that rep by creating some of the world's most iconic timepieces. Here are the ones to own
Published: 18 October 2023

Rolex’s founder, Hans Wilsdorf, was onto something when he made his company logo a crown—it has remained the king of watch brands for more than a century. Its enormous brand equity is partly because Rolex gives so little away, a key to its mystique. It's frequently ranked first in surveys of super-brands in the UK. And is resident in Forbes' list of the world's most powerful brands. Ask 100 people to name a luxury watch and most of them will say Rolex.

This reputation is not mere marketing—Rolex is Rolex because it makes peerless products. We love that so many classic Rolex models were made not just to look good but for specific, adventurous purposes. The GMT-Master, for example, was created for Pan-Am's pilots. Then experiencing a new phenomenon called jet-lag—they wanted a watch that showed two time zones simultaneously.

The Submariner was made for divers. The Milgauss was introduced in the Fifties as an anti-magnetic watch for people working in power plants, medical facilities and early nuclear research labs, where strong electromagnetic fields were present. Collectors are particularly passionate about Rolex sports models, which have long been associated with explorers, adventures and athletes. In addition to the famous James Bond Submariner, an early version of the GMT was worn by US flying ace Chuck Yeager as well as several astronauts.

Rolexes lend themselves to being dressed up and down more than other luxury watch brands. The company mastered the art of the design tweak: collectors wax lyrical over a different coloured bezel here or a bigger crown there. All this contributes to their collectability and value—if you're investing in a watch, buy a Rolex. According to Christie's, Rolexes gain value faster and more steadily than any other brand.

Wilsdorf had a gift for foresight. He bet on the wristwatch very early and each of his major innovations (putting a timepiece on the wrist, making it accurate, making it waterproof and making it automatic) helped create the modern wristwatch as we know it. The downside, some argue, is that Rolex varies its designs even less than other companies: and that’s saying something for the watch world, where a "revolutionary breakthrough" amounts to a new case size or deploying a slightly different type of gold. There is no Rolex tourbillon or sign of the zodiac complication. A 2019 Submariner resembles one from 50 years ago.

The counter-argument is that you don’t go messing with perfection. Instead of visible whistles and bells, the company concentrates on research and engineering, continually update the technology inside its watches on the quiet. A more common grumble is that Rolex’s are so hard to buy right now. Demand outstrips supply, at least for some models, while the aftershocks of the pandemic on supply chains is still being felt. None of this, contrary to one suggestion, is down to Rolex restricting supply.

On the other hand, the thrill of owning a Rolex is also in the chase—if you’re lucky enough to be able to buy one, chances are you’ll remember exactly when and where you were when you did so. In this way there is every reason to believe the Rolex crown will remain firmly in place for another hundred years, and beyond.

Rolex Air-King

Air-King. ROLEX

Often passed by in favour of the Submariner, the GMT-Master or any other of its flashier cousins, the Air-King is a wonderful watch. It is also one of Rolex’ more venerable lines, launched in 1945 as an entry-level model costing less than £100, around a third the price of a Datejust. One of many “Air” watches produced during World War II to honour RAF pilots—see also the long-forgotten Air-Lion, Air-Giant and Air-Tiger—its “King” name related to its size, a then-hefty 34mm—tiny by today’s standards.

The unusual mixing of the large 3, 6 and 9 numerals and the prominent minutes scale isn’t for everyone. Rolex is known for "classic" designs, cry the detractor but we remain firm fans at Esquire. Relaunched in 2022, the Air-King now comes with a redesigned bracelet, Rolex’s latest calibre 3230 movement and a more efficient gear train, giving it 70 hours of power reserve. Bonus trivia: it’s the only Rolex that uses the brand’s gold and green colour scheme.


Rolex Day-Date 36 (2022)

Day-Date 36. ROLEX

Known as the “Presidents’ watch”—a mixed-blessing depending on who’s in charge, Biden took office in a Rolex though has recently become an Omega man—and still a signal you’ve “arrived” for a certain calibre of consumer. The day of the week spelt out in full at 12 o’clock divides opinion among watch snobs but it was no small technical feat when it debuted in 1956. New with an ice blue dial, a feature reserved for Rolex’s ‘950 platinum’ models, the ‘fluted’ bezel is another technical masterstroke, requiring “many years of research” to achieve in platinum, according to the brand.


Rolex Submariner

Submariner. ROLEX

Anyone waiting for Rolex to release a completely new watch could be waiting some time. Rolex’s last new-new model was the Sky-Dweller (2012). Before that, the Yachtmaster (1992) and before that, the Sea-Dweller (1971).

Incremental tweaks to existing watch lines are what Rolex does—a business model that seems to be working out for them. It explains why news of a retooled Submariner, arguably Rolex’s single most iconic design, was one of the biggest watch releases of 2020—even though you’d need a microscope and a degree in horology to spot any updates, the first changes since 2008. (This one’s 1mm bigger, for example.) But the tweaks aren't insignificant. Inside, you get a new calibre (the 3230), an almost 50 per cent increase on the power reserve (up to 70 hours) and the latest escapement. In summing up: a fit-for-purpose 2020 Rolex, and a design classic that will outlive you.


Rolex Oyster Perpetual 36

Oyster Perpetual 36. ROLEX

Red and yellow and pink and green. Also: light blue. Rolex’s new Oyster Perpetual 36 comes in five colourful dials that represent something not always readily associated with the brand: fun. Anyone thinking Rolex has either (a) lost its mind or (b) suddenly decided to chase the youth vote needn’t worry. There is a precedent here, namely the brand’s so-called ‘Stella’ dials: poppy, hard enamel designs that appeared on its Day-Dates as the world turned rainbow-coloured in the early Seventies. They’ve subsequently become hugely sought-after. Watches at 36mm have a broad appeal, and these bright designs offer a welcome point-of-difference for anyone who finds Rolex’s more traditional line-up a tad too traditional.


Rolex GMT-Master II ‘Pepsi’


A GMT Rolex is the ultimate globetrotter’s watch. In 1955, the iconic red and white 24-hour scale on the bezel was introduced. It earned the nickname ‘Pepsi’ (this black and blue version is known as the ‘Batman’). The most recent version in steel adds a state of the art movement and a dressier ‘jubilee’ bracelet. Other than that, the design has changed little in 60 years—though you can file this under timeless, rather than vintage.


Rolex Explorer 40

Explorer 40. ROLEX

Sitting somewhere between a sports and a dress watch, the Explorer 40 was outfitted with calibre 3230, a self-winding mechanical movement entirely developed and manufactured by Rolex. As the name suggests it was made for explorers and comes equipped with Paraflex shock absorbers for a higher shock resistance. But it’s really all about the handsomely proportioned dial, with its period detail numerals and matte finish.

From £6,450

Rolex Sky-Dweller

Sky-Dweller. ROLEX

There are statement watches, and then there’s the Sky-Dweller. The most complicated watch in Rolex’s arsenal, it comes with dual time and annual calendar functions. Previously available on a leather strap or an Oyster bracelet, this newer option comes on an Oysterflex bracelet—Rolex’s patented super-comfy design made up of a titanium and nickel alloy encased in black rubber. Also new is the option of Everose gold or 18k yellow gold. An upscale traveller’s watch might not be at the very top of everyone’s want list right now. But this is a stunning piece of kit to drool over, whatever timezone you happen to be trapped in.


Rolex Oyster Perpetual 41

Oyster Perpetual 41. ROLEX

In a line-up defined by headliners—the Daytona, the Submariner, the Explorer—it would be easy to leave out Rolex’s simplest offering. But if you wanted one watch that would look right with every outfit and in every situation for the rest of your life, that was distinctive without being flashy, this would be it. Though it has been around for decades, the Oyster Perpetual received an update in 2015 that included the a new 39mm case (up from 36mm), an oyster bracelet and an run of hand-finished dials in blue, grape red and dark rhodium.


Rolex Cosmography Daytona

Cosmography Daytona. ROLEX

While you’d certainly be doing well if you stumbled across a vintage Daytona (Paul Newman’s 1968 model remains the most expensive wristwatch ever sold at auction, $17.8m in 2017), if you’re looking for the most advanced chronograph Rolex has ever produced then this recent version is a perfect blend of old and new. The hype, the history—everyone loves this watch.


Rolex Submariner Date

Submariner Date. ROLEX

"Oyster Perpetual Submariner Date in Oyster Steel with Green Cerachrom Bezel and a Green Dial with Large Luminescent Hour Markers". Or, if you prefer: the Rolex Hulk. Introduced in 2010, it immediately fired the imagination of watch fans. The green isn’t just eye-catching, it’s fluid, going from bright to dark green in different light conditions.


Rolex Datejust

Datejust. ROLEX

Probably Rolex’s most popular model. Released in 1945 to celebrate the watchmaker’s 40th anniversary, it also used the occasion to debut a new kind of bracelet—the now-distinctive "jubilee". The first wristwatch ever with a date that changed automatically, the name comes from one of Rolex’s trademark neologisms—the date changes just before midnight.


Rolex Sea-Dweller

Sea-Dweller. ROLEX

When you're saturation diving, down in the depths of the ocean, you've got a lot of things to worry about. You're down there in a pressurised diving bell fretting about giant squid and the like. The last thing you need is your Rolex to give up the ghost. The gas mixture such divers breathe is mostly composed of helium. When helium get into the case they can start pushing it apart from the inside when the wearer returns to the surface. The Sea-Dweller is a companion piece to the Submariner, and arrived in 1967 as its beefier, techier, hardier little brother. The goal was to create a timepiece which could go deeper into the ocean. A smart helium valve in the case to release excess helium made that happen; first certified to 610 metres, then in 1978 doubled it to 1220 metres.


Originally published on Esquire UK

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