No matter how little you know about watches, one thing is universally known and understood: Rolex is king. Culturally, historically, figuratively, hypothetically, literally. It always has been, and it probably always will be. It has the nickname The Crown for a reason, and no one is stealing it from them in a hurry.
Way back in 1905 when ol' mate Hans Wildorf was busy founding Rolex, he said he wanted “to be the first in the field”, and for Rolex to “be seen as the one and only – the best.” Amen to that dogged determination and hindsight. Over the almost-120 years that followed, his vision became a reality. Rolex is perhaps the only watch brand you'd expect everyone to have heard of, and a byword for success.
With that in mind, we figured it worth going through all the best Rolex models and explain what (and who) has helped make each one popular. We asked Brynn Wallner aka Dimepiece, to do the honours. Because, paraphrasing rapper Wiz Khalifa, “Time is money, so it's time to go and buy a Rolex.”
Rolex Oyster Perpetual
The simple, elegant Oyster dates back to 1926 – and might just be the best Rolex ever. It was the first waterproof watch, its name inspired by the tight, sealing properties of an Oyster. A few years later came the term Perpetual, which refers to Rolex’s patented self-winding movement. Conjoined, the term Oyster Perpetual is found across nearly every Rolex dial, indicating that each model is built upon the waterproof Oyster case, fitted with a Perpetual winding automatic movement. But, on its own, the Oyster Perpetual watch is the no-date, steel descendent of the first-ever Oyster.
Got it? OK! With that cleared up, we can discuss the brightly coloured, lacquer dialled OPs that have captivated imaginations and launched a thousand obsessions. Launched in 2020, these trade at least double their retail value and come in flirty hues like candy pink, yellow, coral red… and, of course, Tiffany Blue (not the official name, but we can’t resist). Watch head Kendrick Lamar rocked his (now discontinued, certified grail) 41mm Tiffany Blue OP at the Grammys this year and everyone drooled. To collect each colour is a dream, and capitalising on this, Rolex launched a freshly launched OP “Bubble Dial” dotted with every single colour in the collection. Gotta catch ‘em all!
Rolex Explorer/Explorer II
The Explorer is my favourite Rolex sport watch due to its sheer simplicity. The original reference of this timepiece climbed Everest in 1953, so she doesn't have to flex extra hard with the visuals – she’s an icon and she knows it. The 3-6-9 ("damn, she fine") numbers shine against the strong black dial, making for a minimalist statement that would look great styled with your GORP-core or with Levi’s and a pearl necklace. As famed Explorer owner (and Bond writer) Ian Fleming once said, “A gentleman’s choice of timepiece says as much about him as does his Saville Row suit.” So choose what great men (Fleming, Tom Hardy, literal explorers…) have chosen before you. One last thing: I much prefer the 36mm version of this watch, which is better proportioned and more low-key (and less “try-hard”). Less is more, lads.
Rolex GMT-Master II
At its core, the GMT-Master II evokes the fabulous era of flight before long security lines and Crocs were a mainstay. Its predecessor, the GMT-Master, was born out of PanAm’s request for Rolex to create a pilot watch that could keep up with swiftly shifting time zones as commercial air travel became mainstream. In 1955, the GMT-Master debuted, deploying a rotating bezel and a 24-hour hand to display two time zones simultaneously. Then came the improved-upon GMT-Master II in 1983, boasting a better movement and ability to track a third time zone. So, even if you have a smartphone to tell you the difference between GMT, EST and PST, you can set your watch accordingly to subtly flex your LONDON, NEW YORK, LA jetset lifestyle.
Now, another thing: if you’re new to the watch world and hear people using nicknames for Rolex watches, they’re often in reference to GMT-Master IIs. The “Coke”, the “Pepsi”, the “Rootbeer”, the “Batman”; these are a few names for GMT-Master IIs per their functional bezel colours that cleverly indicate time of day, e.g. the Pepsi’s colours are red for daytime and blue for nighttime. One last thing, at last year’s Watches & Wonders, Rolex debuted a left-handed GMT Master-II (which has since been nicknamed the “Destro”), shaking the earth under Rolex enthusiast’s feet and claiming wrist real estate on notable lefties like NBA's Russell Westbrook and West Ham's Declan Rice.
Rolex Datejust
As common as this watch may seem, the Rolex Datejust is not to be taken for granted. The Datejust was revolutionary when it hit the market in 1945, its automatically changing date window (get it? DATEjust) remaining ever-relevant technology today. In fact, this watch, which initially debuted to celebrate Rolex’s 40th anniversary, holds the title of being Rolex’s best-selling watch of all time. And for good reason! Simple, distinct and versatile, the DJ comes in a countless array of colours, metals and variations. There’s something for everyone, with many collectors calling the Datejust the watch that kicked off their luxury watch collection.
It's difficult to narrow down the amount of star-studded DJ owners… Everyone from Martin Luther King Jr. to Rihanna and David Beckham has worn it. But not, despite popular belief, Christian Bale’s Patrick Bateman in American Psycho; that was a Seiko dupe because Rolex refused to associate with such an evil character. Rolex is scarily on top of its public image, making for an enduring, trend-proof brand that gets entire articles dedicated to its flagship models (like the one you’re reading now).
Rolex Day-Date
In 1957, Rolex unveiled the Day-Date to flex upon itself. Rather than only displaying the date à la the Datejust, this new watch could display the date and the day of the week (get it? DAYDATE!). Adding to the flex, the Day-Date was available exclusively in precious metal (gold or platinum) and came with a new, three-piece link bracelet design, which, with time, came to be known as the ‘President’. This may start ringing a bell… the Rolex “Presidential” is name-dropped in many of your favourite rap songs, initially getting its “head of state” association when it was famously worn by Lyndon B. Johnson (the 36th president of the United States, who stepped in after JFK's 1963 assassination).
Donald Trump wears a Prezzy, too, as does Warren Buffet and other old, rich white guys. But it’s also a go-to for people like Drake, Rihanna, Tony Soprano, Emily Ratajkowski and even… the Dalai Lama. An avid watch collector, fascinated by the passing of time and how things work, his Holiness loves the Day-Date as a reminder to stay present, claiming that “There are only two days in the year that nothing can be done. One is called yesterday and the other is called tomorrow. Today is the right day to love, believe, do and mostly live.” Perhaps this quote inspired Rolex’s latest earth-shattering novelty, the Day-Date “Emoji” watch that replaces dates with emojis and days with affirmation. May your day be “Blessed” and filled with “sunglass emoji” vibes.
Rolex Milgauss
The '50s bore a slew of Rolex tool watches, including the very popular GMT-Master and the Submariner – but a lesser known reference is the Milgauss. One theory as to why the Milgauss hasn’t achieved household name status could be due to the industry it initially aligned with. The GMT-Master was synonymous with air travel, the Submariner with diving – two exceedingly popular fields at the time – whereas the Milgauss was created for… scientists. Although the model itself has evolved since its 1956 launch, the heart of the Milgauss remains the same, intrinsically tied to its name which boasts how many magnetic fields it can withstand: mille (French for one thousand) gauss (a unit of magnetic induction). Anti-magnetism was essential to work in the scientific and technological fields of the day, and Rolex went as far as to partner with CERN (the European Organisation for Nuclear Research) to test these properties. Over 65 years later, the partnership continues today.
Aesthetically speaking, the first iteration of the Milgauss bears more similarity to a Submariner, with the exciting addition of a lightning bolt seconds-hand. From then on, it underwent a few facelifts – with certain references, like '60s minimal Milgauss 1019 becoming beloved in the collecting community – resulting ultimately in 2014’s Milgauss ‘Z-Blue’ we know and love today – with its famous blue-green crystal. With the decline in air travel (sweatpants replacing suits as daily flight wear, exit doors flying off of Boeing 737s), perhaps it’s time we turn science as an industry we can honour with our tool watches, and in this spirit, why not turn to a Milgauss? Tom Hanks – an early adapter – is certainly on board.
Rolex Daytona
The Rolex Daytona was not always the Rolex Daytona. Once upon a time, its ‘50s and ‘60s-era predecessors were relatively overlooked chronographs, lingering in the shadows of Rolex's top selling Oyster and Datejust models. But, like all good fairy tales, Rolex’s flagship chronograph went from zero to hero – thanks in part to its association with fast cars and movie stars. To begin: a chronograph is essentially a stop watch worn on the wrist, so it’s only logical that this would find home on the wrist of race car drivers measuring their laps. As Rolex established itself in the world of motorsport, however, their chronographs weren’t necessarily designed with this in mind.
But then, in 1962, Rolex became the official timekeeper of the Daytona Speedway and a year later created the Cosmograph, built with a tachymeter bezel (allowing the wearer to measure speed or distance in relation to time) and strikingly coloured sub-dials for greater legibility behind the wheel. Internally, the Cosmograph was nicknamed the ‘Daytona’ but the name didn't officially appear on the dial until 1964. By the way, these pre-Daytona Daytonas are highly sought after in the vintage world… But not as sought after as Paul Newman’s ‘Paul Newman’ Daytona. Story has it that Newman – who had a need for speed when he wasn’t on set – was gifted an exotic dial Daytona by his wife, engraved on the back with a sweet suggestion to “Drive Slowly.” This watch, with its white dial and 3 black subdials, became so associated with the actor that it's now known as the Paul Newman. And Paul Newman’s Paul Newman fetched $17.8MM at auction in 2017.
Not all Daytonas will set you back eight figures, but they’re up there and beloved by watch heads du jour like John Mayer, Victoria Beckham and Jonah Hill. And then there’s Jay-Z, who gifted Daytonas in lieu of laminated VIP passes to top donors for his 2019 Shawn Carter Foundation Gala. If only we could go back in time and get a Daytona for that price (~$40K). In retrospect, this was a deal, with the watch in question now trading closer to $60K on the secondary market.
Rolex Submariner
The Rolex Submariner was not the first-ever dive watch, but it was the first watch to enjoy 100m waterproofing. And it is often a collector’s first “tool” watch. A quick bit of context surrounding its release: in the ‘50s, Jacques Cousteau was living the fabulous life aquatic, producing underwater films that pushed Scuba diving into the mainstream and even influenced the design of the Submariner, with its rotating bezel and clean dial. Since it hit the scene in 1953, recreational diving has since gone out of style, but the Submariner has undergone several updates and innovations, sustaining its relevance and desirability.
Some snobily turn up their nose at the Submariner referring to it as, for lack of a better word, basic. And to support this argument, Theo James’s douchey, tech bro character in The White Lotus was styled in the ‘Smurf’ reference of this watch (blue bezel, blue dial). But, to ward off the haters and help destroy the basic label, Al Pacino has been known to rock a Sub. So you make the call, and if you do go with the Submariner, rest assured that it’s built upon 65+ years of history.
Rolex Yacht-Master
Remember when we were talking about the Submariner and adventures under the sea? Well, launching the original Yacht-Master in 1992, Rolex one-upped the Submariner with a watch built to be enjoyed on top of the sea. In a yacht. Indeed, per its name, the Yacht-Master offered something a little more upscale to those looking to kick their feet up on wooden decks, preferring the feel of linen over neoprene. Offered in 18KT white gold (vs the Sub’s humble steel), this watch is decidedly more fancy and has developed to include offerings in other precious metals such as yellow gold and platinum, like the Yacht-Master II, which was released in 2007. Before binding himself to brand deals like Breitling, Brad Pitt wore a Yacht Master, as did cancelled party boy Charlie Sheen (his was the 35mm version). And Nick Jonas was just spotted courtside at Madison Square Garden during a Knick’s playoff game wearing a customised Bamford x Darren Romanelli ‘Popeye’ Yacht-Master.
Rolex Sky-Dweller
Unlike many of the watches listed in this article, the Rolex Sky-Dweller hasn’t been around for decades. In fact, it’s only been around for one! Released in 2012, the Sky-Dweller nevertheless boasts technical prowess and style, which can only be the result of over a century’s worth of Rolex R&D. Here, the Sky-Dweller name is not used to describe a pilot, but rather a world traveller. The ‘50s produced GMT-Masters for pilots; but in 2012… Think about it. Pilots had computers for in-flight timekeeping, and any watch on the wrist is purely ornamental. So, the Sky-Dweller was built for modern travel, featuring a complex dial that, however busy it may be, conveys an intuitive dual time-zone. Rolex was perhaps having a bit of fun when they developed this watch, riding high off the flashy y2k energy that preceded its release.
The y2k vibe can also explain its size, which clocks in at a hulking 42mm – en vogue at the time, and rather bulky compared to the smaller-leaning, vintage inspired trend we’re currently exploring. And yet despite its humble lifespan and high millimetre count, the Sky-Dweller remains a status symbol for those brave enough to rock it. Tom Cruise wears one, as does Jack Harlow. Then there’s Michael Jordan and LeBron James, who both wear it proudly. If it’s good enough for the GOATs…
Rolex Air-King
The first commercially available Rolex Air-King debuted in 1958, hot off the heels of the GMT-Master. These were the glory days of smoking cigarettes in first class PanAm seats. But the original Air-King came about during the 1930s “Golden Age of Flight”, when pilots were honing aircraft engineering and commercial flight existed only in their imaginations. The original Air-King featured enlarged 3, 6 and 9 numerals (much like the Rolex Explorer), rendering its dial legible mid-flight, but was far simpler in build than the GMT-Master. Now, celebrating its 65th year, the Air-King has undergone several evolutions; but you may recognise the name from its association with the now certified-grail Domino’s Pizza Rolex.
These are simply Air-Kings customised with the Domino’s logo, gifted to top earners within the company. During the time, somewhere in the ‘80s and ‘90s, the Air-King was known as a ‘starter Rolex’ with an $800 price tag, and yet this was enough to incentivise employees. Now, these Domino’s Air-Kings are sought after amongst a whimsically-minded type of collector and have skyrocketed in value on the secondary market, trading for as high as $19K. That’s a lot of dough!
Rolex 1908
If you’ve made it this far in this article, you may have noticed a pattern – most of these heavy-hitter pieces are tool watches – built for sport, built for industry, built real tough. The Day-Dates and the Datejusts might look good with a suit, but you may find yourself asking ‘What if I want a proper dress watch?’ The discontinued (and underrated) Rolex Cellini is a good option – but the Crown has another proposal: the vintage-inspired Rolex Perpetual 1908, which debuted at Watches & Wonders in 2023 and was quickly snapped up by Roger Federer. Named for the year Hans Wilsdorf registered the Rolex trademark in Switzerland, the Perpetual 1908 checks all the dress watch boxes (classy, time-only, precious metal, leather-strapped) with the bells and whistles of modern Rolex (namely the exhibition caseback that shows off the ultra slim, very efficient automatic calibre 7140 movement). At £19,300, the 1908 provides good value for collectors looking to class up their repertoire – and for those of us not willing to drop tens of thousands of dollars, the 1908 should provide good inspo to dig into Rolex’s discontinued dress watches. You’d be surprised at the sheer variety that falls under the Cellini line, ranging from simple leather-strapped offerings to wild, jewellery-forward pieces apt for the brave standing proudly in opposition to the “stealth wealth” trend.
