The 21 Best Rolex Watches of All Time

Rolex are Rolex. We all know them, so many of us love them, and it’s all for good reason. They’ve become the ultimate symbol of style, success, and craftsmanship, and that doesn’t change if you’re a die-hard collector or just someone who appreciates a great watch.

Why is Rolex so special? That’s not an easy question to answer in a few sentences. But they’ve somehow mastered the art of precision, durability, and timeless design, so timeless in fact that Rolex watches will effortlessly take you from an adventurous underwater situation to something formal in a boardroom.  

But with a successful history comes options, and with over a century under this Swiss watchmaker’s belt, there are many Rolex watches out there to consider.

You have the Submariner, the Daytona, the Datejust and so many more, each with their own set of unique characteristics and story. So how do you choose? Well a good place to start is right here, exploring some of the best Rolex watches of all time.

How To Choose the Right Rolex Watch For You?

Before we get into the best Rolex watches of all time, first take a moment to consider what you want in a watch. Because at the end of the day, the perfect Rolex isn’t just about picking the most popular model but about finding the one that best suits you.

There are a few key things to consider like budget, style, sizing, and design preferences. Rolex watches are an investment, and while prices vary, even the most affordable options come with several zeros on the price tag to make up for that craftsmanship and prestige.

It’s also worth noting that Rolex is a brand built on timeless design. Their DNA has changed very little over the decades, and rightly so because they nailed it from the start.

Most models exude a classic, enduring style that never goes out of fashion so if you want something overly bold and funky, a different brand might be a better option. Although don’t leave just yet, because Rolex do have a small handful of bold exceptions you’ll see later.  

It’s also true that different Rolex families are designed with specific environments in mind like the diving-inspired Submariner, the motorsport-driven Daytona, and the adventure-ready timepieces like the Explorer. But that doesn’t mean you need to be a diver to wear a Submariner, nor a motorsport enthusiast to rock a Daytona.

At the end of the day, choose the watch that speaks to you, offers the functionality you want, and has a style you’ll throw on effortlessly every day. The best Rolex for you is the one that brings you joy every time you glance at your wrist.

The 20 Best Rolex Watches of All Time

With so many iconic Rolex models out there, narrowing it down to the best of the best is no easy task. But that’s exactly what we’ve done here. Whether you’re into classic dress watches, legendary tool watches, or statement-making timepieces, we’re pretty confident there’s a Rolex watch down below that’s going to suit you.

Rolex Submariner

In the top spot, unsurprisingly, we have the Rolex Submariner. This isn’t just one of the best Rolex watches of all time, but it might just be one of the most important watches ever. Since its debut in 1953, the Submariner has shaped the entire world of dive watches and set the standard for what a luxury sports watch should be.

Its appeal is universal. The Sub has been on the wrists of explorers, divers, celebrities, and even James Bond cementing its place as a true icon. It’s rugged yet refined, designed for the deep sea but just as at home under a suit cuff. Over the decades, it has seen updates in materials, movements, and case proportions, but the core design remains as timeless as ever.

Rolex Oyster Perpetual

Before anything else, it’s important to clear up a common misconception. The words Oyster Perpetual appear on almost every Rolex, but here we’re talking about the actual watch model, not the technology behind it.

Oyster refers to Rolex’s famous waterproof case from 1926, while Perpetual represents the automatic movement introduced in 1931. Together, they make up the foundation of Rolex watchmaking.

The Oyster Perpetual itself is as classic as it gets. No date window and no complications; it’s just a clean, refined, and highly versatile design. For years, it was seen as a quiet classic rather than a headline grabber, but that changed in 2020.

New dial colors including vibrant turquoise and bright pink, along with a larger 41mm case option, has made it an instant favorite among collectors. The playful “Celebration” dial pushed things even further and has proved that Rolex can be bold when they want to be.

Rolex Explorer

When Sir Edmund Hillary and Tenzing Norgay became the first climbers to reach the summit of Mount Everest in 1953, they carried a Rolex Oyster Perpetual with them. Inspired by this historic achievement, Rolex launched the Explorer later that year, cementing its place as the ultimate go-anywhere, do-anything watch.

Seventy years later, the Explorer remains largely unchanged and that’s exactly why people love it. The 36mm case, clean black dial, and bold 3-6-9 numerals make it one of the most versatile watches Rolex has ever created.

It’s sleek enough for the office yet rugged enough to withstand extreme conditions. The Rolex Explorer reference 1016, a model that has been produced for nearly three decades, remains one of the brand’s best-known cult favorites.

Rolex Explorer II

The Explorer II takes everything great about the original Explorer and dials up the adventure factor. While the Explorer I is all about simplicity, the Explorer II adds a bold, functional twist with a 24-hour hand and fixed bezel designed to help wearers distinguish between day and night.

But interestingly, the bezel doesn’t rotate, and in earlier versions, the 24-hour hand was linked to the main time, rather than independently adjustable so it’s not your standard GMT watch.

It’s a model ideal for cave explorers, polar adventurers, or anyone spending long periods in environments where the sun doesn’t rise or set. But let’s be honest not many people buying an Explorer II today are actually using it for spelunking.

What keeps this watch in high demand is its rugged, sporty design, larger case size, and that eye-catching orange hand, which gives it just the right amount of flair.

Rolex GMT-Master

The Rolex GMT-Master isn’t just a sharp-looking watch that’s also a large part of Rolex’s aviation history. Back in the 1950s, when long-haul flights were becoming a reality, Pan Am needed a timepiece that could track two time zones at once for its pilots. Rolex delivered, and in 1955, the GMT-Master was born, complete with a 24-hour bezel and an extra hour hand to track a second time zone.

The first-ever ref. 6542 came with a fragile Bakelite bezel, which Rolex quickly swapped for aluminum. By 1959, the legendary ref. 1675 arrived, bringing a larger 40mm case, crown guards, and the first COSC-certified movement in the series.

The GMT-Master I is no longer in production, but it remains highly sought-after, especially classics like the ref. 1675, which has been a collector’s favorite – albeit an expensive favorite – for many years.

Rolex GMT-Master II

The Rolex GMT-Master II took everything great about the original GMT-Master and made it even better. While the first GMT-Master is now discontinued, the GMT-Master II remains in production, proving just how popular and enduring this model is.

At first glance, the two watches look nearly identical, but the biggest upgrade came in 1983 when Rolex introduced a movement that allowed the 24-hour hand to be set independently from the main hour hand.

This simple tweak meant wearers could now track three time zones instead of two, one on the main dial, another with the 24-hour hand, and a third by rotating the bezel. It’s still one of Rolex’s hottest and hardest-to-get watches, especially in stainless steel, while older, discontinued versions offer great investment potential.

Rolex Datejust

The Rolex Datejust might not be the flashiest watch in the lineup, but it’s the backbone of Rolex’s success and one of the most instantly recognizable timepieces ever made. It debuted in 1945 to celebrate Rolex’s 40th anniversary and became the world’s first watch with a self-changing date window, setting the standard for modern date complications. It also brought us the Jubilee bracelet, an alternative to the sportier Oyster bracelet that adds a little extra refinement to the mix.

For many, the Datejust is their first Rolex since it’s the perfect blend of affordability, versatility and history. And while it may not grab headlines like the Explorer or Submariner, its everlasting appeal keeps it firmly at the heart of Rolex’s catalog proving that sometimes, the classics never go out of style.

Rolex Lady Datejust

Some of you might think this one’s a bit high on the list, but hear me out. The Lady-Datejust absolutely deserves its spot. As mentioned above, the classic Datejust has been a Rolex staple since 1945, and just over a decade later, in 1957, Rolex introduced a version tailored specifically for women.

Same iconic design, just in a more compact size. And while it might not get the same hype as some of Rolex’s better known sports models, by volume, it outsells many of them.

The Lady-Datejust keeps everything that made the original great like the Oyster case for water resistance, the self-winding movement, and that signature date window at 3 o’clock.

It just offered a much more compact design for those with smaller wrists. It’s a collection that also offers insane levels of variety with the case available in every metal finish, from Oystersteel to Everose gold, platinum, and even two-tone Rolesor models.

Rolex Day-Date

If this list were purely based on dream watches, the Rolex Day-Date would be sitting right at the top for me. There’s just something about it. It has the perfect blend of luxury, prestige, and practicality. It’s not quite a sports watch, but it’s not strictly a dress watch either.

The Day-Date made history when it launched in 1956 as the first watch to display both the date and the full day of the week. It also arrived with the legendary President bracelet, which debuted on this model and went on to earn the watch its famous “Rolex President” nickname. That nickname was also cemented by U.S. Presidents Lyndon B. Johnson, JFK (rumored, at least) and Ronald Reagan who had their own.

Rolex Daytona

The Rolex Daytona is the only chronograph in the Swiss watchmaker’s lineup and has become a symbol of the brand’s deep-rooted connection to motorsports. Since its debut in 1963, the Daytona has gone from a tool for race car drivers to one of the most coveted, valuable, and recognizable watches in the world.

If there’s one watch that defines vintage collecting, it’s the Paul Newman Daytona, a version of the ref. 6239 with an exotic dial that became legendary thanks to the actor and racing enthusiast himself. His personal watch sold for $17.8 million in 2017, setting the record for the most expensive vintage wristwatch ever sold.

That moment single-handedly launched the Daytona into another stratosphere of desirability. But even beyond vintage models, the modern Daytona is a grail piece for many collectors. Try walking into a Rolex boutique and asking for one and  you’ll be met with years-long waitlists or a hefty price tag on the pre-owned market.

Rolex Perpetual 1908

The Rolex Perpetual 1908 launched in 2023 and quickly became Rolex’s answer to those seeking a sophisticated, dressier timepiece. With its sleek 18k yellow or white gold cases and minimalist black or white dials, it filled the gap left by the discontinued Cellini collection.

The watch features a subtle railroad track printing, applied markers, and Breguet-style hands, blending modern design with vintage elegance.

In 2024, Rolex introduced a platinum version with a stunning “rice-grain” guilloché pattern and a cool icy-blue dial, taking the Perpetual 1908 to new heights of luxury. Still young, this collection shows promise as one of Rolex’s most refined dress watches in years, offering an elegant balance of classic charm and modern precision.

Rolex Yacht-Master

The Rolex Yacht-Master, introduced in 1992, is another of Rolex’s well known sports watches. Designed with the boating community in mind, hence the name, it combines a sleek, diver-inspired aesthetic with high-end materials like gold and mother-of-pearl. Initially crafted from 18k yellow gold, it soon expanded to include a variety of metals and sizes, giving it widespread appeal among collectors.

Rolex’s Yacht-Master II came later, launching in 2007 and elevated the design with an additional regatta timer designed specifically for competitive sailing. It’s a Rolex all about precision and timing, making it a tool for sailors rather than casual enthusiasts. Although of course, you don’t have to be on board a boat to appreciate its design.

Rolex Sea-Dweller

While the Submariner is a great everyday dive watch, the Rolex Sea-Dweller is built for those who truly want to push the limits of underwater exploration. Introduced in 1967 for saturation divers, it offers more than triple the water resistance of the Submariner and features a helium escape valve to prevent crystal issues during decompression.

The most popular Sea-Dweller is without doubt the Deepsea reference worn by James Cameron during his Mariana Trench dive. It’s a watch with an astonishing 3,900 meter water resistance. Modern-day references continue to be a symbol of technical achievement and durability, whether it’s the larger 43mm case in 2017 or the luxurious Yellow Rolesor Sea-Dweller which joined in 2019.

Rolex Air-King

The Rolex Air-King, introduced in 1945 to honor RAF pilots from WWII, is one of the longest-running models in Rolex’s catalog. Initially a dress watch, it has evolved into a more rugged, professional tool watch. The modern version, revamped in 2022, features a 40mm case and a dial inspired by cockpit instruments, giving it a distinctive, utilitarian feel.

The Air-King’s legacy includes a variety of design updates over the years, from engine-turned bezels to concentric dials, but the most recent version seems to have struck the right balance. With its understated elegance, green accents, and aviation roots, it’s a watch that offers both historical significance and a unique place within Rolex’s professional tool watch lineup.

Rolex Cellini

The Rolex Cellini line sadly no longer exists, debuting in 1968 as the brand’s attempt to enter the world of luxury dress watches – something which was far removed from their tool-watch reputation. The Cellini was crafted with refined designs, precious metals, and sometimes even gemstones, making it the perfect choice for black-tie occasions. It was also pivotal in helping Rolex shift its brand identity, with a focus on luxury as much as functionality.

While the Cellini may not have received the same widespread affection as Rolex’s sportier models, it was an essential piece in the brand’s collection. Named after the Italian goldsmith Benvenuto Cellini, the line highlighted impeccable craftsmanship and elegance. The Cellini was also favoured by influential figures like former President Barack Obama, cementing its place as a symbol of understated luxury. Sadly, this historic line has come to an end, leaving behind the aforementioned Rolex 1908.

Rolex King Midas

The Rolex King Midas is undoubtedly one of the brand’s boldest and most unique creations. Released in 1964, this asymmetrical, 18k gold watch was designed by Gérald Genta (the very man behind the Audemars Piguet Royal Oak and Patek Philippe Nautilus) and became the heaviest gold watch of its time.

With its chunky bracelet, crafted from a single block of gold, and its unconventional urn-shaped case, the King Midas was both a luxury piece and a statement of artistic design.

For a while, it was also the most expensive Rolex available and its exclusivity was underscored by its limited edition status. Famous owners like Elvis Presley and John Wayne continued to cement its value. The King Midas was eventually absorbed into the Cellini line and was later discontinued but it still remains one of Rolex’s most intriguing and rare models.

Rolex Oyster Perpetual Milgauss

The Rolex Oyster Perpetual Milgauss was introduced in 1956 to cater to professionals working in environments with strong electromagnetic fields, like scientists, engineers, and doctors. Before its release, traditional watches would lose accuracy in high magnetic fields, but the Milgauss was designed to resist up to 1,000 gauss which was a significant breakthrough in horology at this time.

Initially tested at CERN, the watch quickly became a vital tool for those in the scientific community with its most distinctive feature being the lightning-bolt second hand, a nod to its scientific roots.

The Milgauss had a brief early history with models like the ref. 6541 and ref. 1019, and was later revived in 2007, with the most recent version featuring a unique green-tinted crystal. But it was discontinued again in 2023, and thus remains a rarity, making it a popular one with collectors.

Rolex Oysterquartz

The Rolex Oysterquartz was Rolex’s entry into the quartz revolution during the 1970s, a period marked by the rise of electronic timekeeping. Rolex spent five years developing its own quartz movement, and the result was a luxury watch that combined Rolex’s precision with the new-age technology of quartz.

Produced from 1977 to the early 2000s, the Oysterquartz is a quintessentially ’70s piece, featuring angular cases and integrated bracelets, reminiscent of the era’s design trends seen in watches like the Royal Oak and Nautilus.

The Oysterquartz was available in two main lines, the Datejust and Day-Date, with cases typically measuring 36mm. Despite being produced for 25 years, fewer than 25,000 Oysterquartz watches were ever made, making them relatively rare compared to Rolex’s other offerings.

While often overlooked today, the Oysterquartz remains a fascinating chapter in Rolex’s history, showcasing their commitment to innovation during a pivotal time in the watch industry.

Rolex Prince

The Rolex Prince is perhaps one of the brand’s most unexpected models, and it offers an intriguing glimpse into Rolex’s early innovation.

Introduced in 1928, the Prince was a rectangular watch with a distinct Art Deco design, and while it was intended for elegant, black-tie occasions, it became particularly popular with a specific group of professionals: doctors.

The Prince featured a seconds sub-dial that allowed medical professionals to measure a patient’s heartbeat, making it an unusual but highly practical tool for healthcare.

The original Rolex Prince was discontinued in 1940, but Rolex revived it in 2005 as part of the Cellini collection, before retiring it again in 2015. It’s definitely not the most famous Rolex watch, but it’s a fascinating example of a model built for function and style, and still an important piece of Rolex history.

Rolex Sky-Dweller

The Rolex Sky-Dweller, introduced in 2012, was designed to compete with luxury travel watches like the GMT-Master but with a more sophisticated, flashy twist.

While the GMT-Master catered to pilots, the Sky-Dweller was aimed at high-end travelers, offering a stylish 42mm case, mostly in precious metals like gold. It was a departure for Rolex, as it didn’t have a rich historical lineage to draw from, allowing the brand to create a completely new design.

Some of its most notable features include the Ring Command bezel which allows the wearer to adjust the month, date, and two time zones easily and the annual calendar and GMT complications.

It feels like Rolex is still writing its history on this one, since it’s still relatively new to their portfolio compared to so many of their other references, so who knows where its popularity will go.

Rolex Pearlmaster

The Rolex Pearlmaster was introduced in 1992 as the brand’s ultra-luxury, diamond-adorned variation of the Datejust. Exclusively crafted in precious metals, it featured an eye-catching, opulent design with a mirror-polished case and bracelet, adorned with at least 12 diamonds or gemstones.

It was initially offered in smaller sizes of 29mm and 34mm before eventually including some 34mm and 39mm versions.

This is a Rolex that was never a mainstream hit but garnered attention for its extravagant nature, appealing mostly to celebrities and the ultra-wealthy who appreciated its high jewelry aesthetic. For 30 years, the Pearlmaster stood as Rolex’s most flamboyant offering, with its bling-filled design eventually being integrated into other Rolex models.

It was eventually discontinued in 2022 but continues to live on as a symbol of Rolex’s brief flirtation with ultra-flashy, gemstone-studded timepieces.

Rolex Oyster Perpetual True Beat

Finally, we have the Rolex Tru-Beat. This is a watch introduced in 1954 and is something of a fascinating anomaly in watchmaking history. Featuring a “deadbeat” seconds hand, it ticks once per second, just like a quartz watch, but with the mechanical precision Rolex is known for. This rare complication was designed specifically for medical professionals to measure a patient’s pulse rate more easily.

The Tru-Beat’s mechanism was incredibly complex, as it had to slow down the usual sweeping motion of a mechanical movement to advance the seconds hand just once every tick. Despite its innovative design, the Tru-Beat was a niche product with limited appeal, and Rolex only produced it for five years. Consequently, the Tru-Beat is one of the rarest Rolex models, often commanding high prices when found at auction.

Conclusion

With so many incredible Rolex models out there, each offering something different from the next, choosing the right one can feel like an impossible task. Some models have been discontinued and are now only available on the second hand market, while others are so in demand that the waiting lists stretch for years.

But at the end of the day, the best Rolex isn’t just about rarity or price but about what speaks to you. Whether you’re drawn to a classic design like the Datejust, the rugged appeal of the Explorer, or the prestige of a Daytona, the best Rolex is the one that fits your style and lifestyle. Find the one that tickles your wrist in just the right way, then go out and make it yours. It won’t be cheap, but it’ll be worth it.