The Best Rolex Watches for Collectors and the Stories Behind Them

Rolex watches are indisputably some of the most popular and coveted timepieces on the planet, and every watch enthusiast has their own ideas about (and often their own criteria for) what the best Rolex watches are. But how much do you really know about how your favorite Rolex model came about, why exactly it's so special and distinct from all the rest, and in some cases why it is historically significant to the watch industry as a whole? In this feature, we take a tour through nine of the most important and/or interesting Rolex watches, from their original conception to their place in the modern horological canon. 

Origins of an Icon

The most famous Swiss watch brand in the world was originally not even Swiss: it was founded by a German in the United Kingdom. Hans Wilsdorf (1861-1960), an orphan raised by his uncles in Kulmbach, Germany, learned entrepreneurship and self-sufficiency early in life, and began his career in the Swiss watch industry in 1900 when he started as a clerk at the watchmaking firm of Cuno Korten in La Chaux-de-Fonds, responsible for the maintenance and accuracy of hundreds of pocket watches per day. In 1905, two years after moving to London, Wilsdorf (below) partnered with another businessman named Alfred Davis to establish Wilsdorf & Davis, the company that would become Rolex. Wilsdorf & Davis, based in London’s Hatton Garden commercial district, was founded with a mandate to make reliably precise watches at affordable prices. 

In 1914, days before the outbreak of World War I, Wilsdorf changed the name of the company to “The Rolex Watch Company Ltd.” and shortly thereafter shifted its focus from pocket watches to “wristlets,” or wrist-worn watches. Wilsdorf, an early believer in the commercial potential of wristwatches, would later state in an autobiography that the name “Rolex” came to him via a “genie” whispering in his ear while he was running an array of different alphabetical combinations through his mind during a horse-drawn carriage ride through London. As many would note thereafter, it was also a brand name that was easy to spell and to pronounce in many languages while also being short enough to fit elegantly on a watch dial.

Oyster Meets Perpetual

Almost immediately upon this reinvention of his company, Wilsdorf set his mind toward tackling a challenge that had plagued watchmakers for the first decades of their existence: developing a case that could withstand being submerged in water. In 1926, Wilsdorf introduced the first Oyster case, whose innovative design combined a threaded, hermetically sealed caseback and a crown that screwed securely into the side of the case for a water resistance never before achieved in watches. It took its name from the bivalve mollusk whose traits it emulated, except that its function was the opposite, with the two “shells” of the case clamping tight to keep water outside, rather than inside. The first Oyster watches, released that year (example above), took their name from the groundbreaking invention. One year later, in what would become the first of many celebrity-driven marketing initiatives over the years, Rolex partnered with Mercedes Gleitze, a British professional swimmer, for a widely publicized campaign. Gleitze wore a Rolex Oyster on a necklace during her first (unsuccessful) attempt to become the first woman to swim the English Channel. The watch was still ticking when she returned to shore, allowing Rolex to tout the waterproofness of its watch in a big way in subsequent advertisements. 

Rolex watches had already become renowned for their accuracy, having won chronometry competitions as early as 1910. In 1931, Wilsdorf’s other quest came to fruition with the development of a patented, self-winding movement with a weighted mass that served to wind the mainspring via the motion of the wearer’s arm. Because this type of movement (above) kept the watch constantly wound as long as it was being worn, it was referred to, then and now, as “Perpetual.” It wasn’t the first self-winding, or “automatic” movement in a wristwatch — that would be the one patented by British watchmaker John Harwood in 1923 — but it was a development that spurred other watch manufacturers to begin adopting the technology in their own products. Most of Rolex's most popular models today fall under the Oyster Perpetual banner, including the watches showcased here, each representing a historically important pillar of Rolex's collection while offering its own singular charm. 

Best Rolex Watch for Everyday Elegance:

Rolex Datejust (1945)

Perhaps surprisingly to those of us who follow the breakneck pace of advancements in today’s watch world, it took more than a decade for Rolex to offer both the robustness of the Oyster case and the convenience of the Perpetual movement in a single timepiece. The Rolex Datejust, unveiled in 1945, was the first Rolex watch with the now familiar phrase “Oyster Perpetual” spelled out on the dial. The watch was also the first to feature the now-ubiquitous date display at 3 o’clock, the first automatic watch with a quick-change function for that date display, and the first to be mounted on Rolex’s now-famous five-row Jubilee bracelet. A few years later, in 1948, came the first Datejust with the bubble-shaped “Cyclops” lens directly above the date aperture, which magnified the date numeral by a factor of 2.5 for greater legibility at a glance. Rolex filed for a patent on the Cyclops lens in 1952. Legend has it that Wilsdorf came up with the feature after his second wife lamented to him how difficult it was for her to read the date on her watch, and that the idea came to him after a droplet of water fell onto his watch’s crystal over the date window while he was washing his hands in the bathroom. 

The first Datejust (Ref. 4467), originally only offered in yellow gold and containing the chronometer-certified, self-winding Caliber A295, established the familiar aesthetic of the Datejust models, most notably the fluted bezel and clean, elegant dial with triangular indexes. The earliest models used a bright red numerical font for the date, an element that was eventually abandoned as the Cyclops lens became common throughout the line. The Datejust has been a mainstay in the Rolex collection ever since, retaining its 36mm case size and upgrading over the years to more advanced movements as Rolex continually upgrades its technological savoir-faire. In 2009, Rolex introduced the Datejust II (since superseded by the Datejust 41 in 2016), which features an expanded case size of 41mm and contains Rolex’s in-house, COSC-certified perpetual Caliber 3136 inside its 100-meter water resistant case. 

Best Rolex Watch to Start Your Collection:

Rolex Air-King (1945)

Released the same year as the Datejust was a trio of timepieces that celebrated the accomplishments of Britain’s Royal Air Force in the wake of the Allied victory in World War II. (Wilsdorf had moved Rolex’s headquarters to Geneva, Switzerland, in 1920 due to unfavorable economic conditions in the U.K., but the company retained an affinity for its British roots.) The so-called “Air Series” comprised two models that are long discontinued, the Air-Giant and Air-Tiger, and the one that is still being produced, the Air-King (vintage example above). Despite being the oldest continuously produced model in Rolex’s star-studded lineup, the Air-King has never attained the levels of mainstream popularity and collectability enjoyed by household-name watches like the Daytona, Submariner, GMT-Master, and others, but it remains for many a very desirable “entry-level” Rolex watch due to its history and its affordable price relative to those other models. 

The Air-King, originally designed “to honor the pioneers of aviation,” has undergone a number of evolutions throughout the years. The original model’s 34mm case (considered large at the time, believe it or not), cream-colored dial and manual wind movement would eventually be replaced by the now-familiar design that was revamped in 2016: a black dial with a 60-minute scale and inverted triangle at the 12 o’clock/60-minute position (a feature of historical pilots’ watches); large 3, 6, and 9 Arabic numerals at their respective positions; and a retro-font “Air-King” logo slightly below center.of the “Mercedes”-style handset. In 2022, Rolex updated the Air King further, adding crown guards to its 40mm case for increased sturdiness as well as consistency with its siblings in Rolex’s Professional line; an upgraded movement, the automatic, in-house Caliber 3230; and most notably the double-digit “05” applied numeral on the dial’s scale to replace the single-digit “5” that preceded it, for an even more streamlined look. More on the 2022 revival of the Rolex Air-King here.

Best Rolex Watch for Outdoor Adventure:

Rolex Explorer (1953)

The Rolex Explorer is known chiefly as the watch that was worn by Sir Edmund Hillary and Tenzing Norgay on their historic expedition to the summit of Mount Everest in 1953, the same year the watch debuted. The model’s aesthetic roots reach back farther, to the 5020 “Ovettone” series of watches that Rolex made in the 1940s. The nickname “Ovettone,” Italian for “big egg,” referred to those watches’ monobloc Oyster cases, which were not only larger than usual for the time (36mm, at a time when most men’s watches, including those from Rolex, averaged 32mm to 33mm). They were also notable for their domed casebacks (called “bubbleback” and necessitated by the thickness of the perpetual movement inside them at the time) and crystals. The successor 6298 series, with three-part cases replacing the monobloc ones, are today considered the prototypes for the modern Rolex Explorer. The watch that Rolex actually provided for Hilary and Norgay’s mission was the “pre-Explorer” Ref. 6098, equipped with the automatic Caliber A296, which was never produced commercially, but the worldwide fame garnered by the successful summit provided all the marketing juice that Rolex needed for the launch of the mountaineering-themed timepiece that it released that year, Ref. 6350 (above), the first “official” Rolex Explorer. (Much more detail on the watch and its origins can be found here.) 

It was the preceding Ref. 6150, which didn’t have “Explorer” printed on the dial, which nevertheless established the emblematic Explorer dial layout: inverted triangle at 12 o’clock, numerals at 3, 6, and 9 o’clock, Mercedes-style hour hand and pencil-shaped minute hand, and bar indexes at the other hour positions. Its steel case measured 36mm, like those of the watches carried on the Everest expedition. The Ref. 1016 that followed shortly thereafter is the longest-lasting of the Explorer references, worn by many enthusiasts over its decades of production including James Bond creator Ian Fleming (below). In fact, that reference is considered by some Bond nerds to be the “real” James Bond Rolex watch rather than the Submariner (which we’ll explore below), since Fleming described 007’s watch in the novels with attributes very similar to those of his own personal Explorer.

In 1971, Rolex launched a version of the Explorer with a GMT function, naming it the Explorer II, thus retroactively making the original three-hand model the Explorer I. Rolex produces only two versions of the Explorer I in its current collection, one in all-steel (Rolex calls its “Oystersteel”), the other in the brand’s steel-and-gold “Rolesor” combo, both with the original 36mm case dimensions.

Best Rolex Watch for Divers and Strivers:

Rolex Submariner (1953)

Rolex’s history in the field of diving and waterproof watches is long, prestigious, and far too rich to sum up here. However, no single timepiece embodies that history more eloquently than the Submariner, a watch that treads the line between tool watch and luxury totem more deftly than just about any other model in modern horology. Like other Rolex icons, the Submariner (vintage model pictured above) originally came as a response to consumer demand brought about by a cultural shift. After World War II, diving had evolved to become a recreational and commercial pursuit rather than strictly a military skill set, and Jacques Cousteau’s historic invention of the Aqualung ensured that this new generation of recreational divers could remain underwater for longer periods. Thus, a new type of watch was needed that enabled a diver to keep track of his air supply. 

Rolex, which had already pioneered the waterproof Oyster case, and had built the first military-issued dive watches for the Italian firm Panerai in the 1930s and ‘40s, was one of the first watchmakers to respond to this demand in the seminal year of 1953, along with Blancpain and Zodiac. The first Submariner was Ref. 6204, which established the template for the model — 37mm steel Oyster case, black dial with inverted triangle at 12 o’clock, alternating circle and bar indexes at the hour markers, and a unidirectionally rotating bezel with a 60-minute scale that a diver could set to keep track of his time underwater. The Submariner was touted as the first watch that was waterproof to 100 meters — a significant claim, as the other iconic dive watch that had preceded it to market, the Blancpain Fifty Fathoms, was tested only to the 91.44 meters that matched up to its name. Subsequent references of the Submariner, starting with the Ref. 6205, added the familiar Mercedes handset and even more robust water-resistance ratings, of 200 meters, and eventually 300 meters, which is the standard for the model today. The first models were equipped with the automatic A260 caliber; today’s Submariners contain Rolex’s Caliber 3235, which offers chronometer-certified accuracy and reliability as well as a power reserve of 70 hours. 

As alluded to above, many fans of the Rolex Submariner still regard it as the original “James Bond Watch.” Sean Connery wore one, specifically a Ref. 6538, in the first three Bond movies from 1962 to 1964. The watch's association with the suave superspy undoubtedly aided in its transition from pure sport watch to sport-luxury icon over the years. Rolex, however, continued to challenge the frontiers of underwater endurance even as its groundbreaking dive watch was going mainstream. In 1971, Rolex introduced the Sea-Dweller, a larger and even more heavy-duty version of the Submariner that was aimed at professional saturation divers; its case was depth-tested to an astounding 610 meters and fitted with an automatic helium release valve to aid in decompression; today’s Sea-Dweller tops out at a bone-crushing 1,200 meters of water resistance. The Rolex Deepsea Sea Dweller, introduced in 2008, shattered even this record with its water-resistance rating of 3,900 meters. 

Best Rolex Watch for World Travelers:

Rolex GMT-Master (1954)/GMT-Master II (1983)

Like the Submariner that had preceded it, the Rolex GMT-Master was both trend-setting and genre-defining in its now-iconic conception. The original GMT-Master (Ref. 6542, above, which actually hit the market in 1955) was the first watch capable of displaying the time in two separate time zones thanks to the clever addition of a fourth, central 24-hour hand and a bidirectional rotating 24-hour bezel. The initials in the watch’s name signify “Greenwich Mean Time,” the system of world timekeeping based on the calculation of mean solar time from the Royal Observatory in Greenwich, London. Notably from an aviation history perspective, its dual-time functionality was an innovation devised for, and developed in cooperation with, the original watch’s intended users: pilots for Pan American Airlines, at the time one of the U.S.A.’s leading commercial carriers. In that so-called Golden Age of commercial aviation, the growth of long-haul and international flights prompted the desire for a tool watch that enabled a pilot to track the time in both his home city, and his flight’s destination city, anywhere in the world. 

While other watch manufacturers, before and since, have established various ways of displaying and tracking two or more time zones, it is Rolex’s design that has proven the most impactful and enduring, and the one most emulated by other brands looking to entice world travelers. The first-generation GMT-Master Ref. 6452 — which was based in part on the Datejust Turn-o-Graph, Rolex’s first watch with a rotating bezel — had a 38mm steel Oyster case, a black dial with the hallmark “Mercedes” handset, a 3 o’clock date window under a Cyclops lens, and most remarkably from a historical standpoint, a bidirectional bezel graduated to 24 hours and divided into two equal sectors of red and blue, a clever and eye-catching visual shorthand to identify daytime and nighttime hours on the 24-hour scale. This red-and-blue “Pepsi” bezel would herald other popular colorways with pop-cultural nicknames, like the red-and-black “Coke” bezel on the Ref. 16760 model in 1983 and the blue-and-black “Batman” bezel of the Ref. 116710BLNR in 2013. The former model represented the first generation of the GMT-Master II, which boasted an independently adjustable GMT hand along with the rotating GMT bezel, allowing for the display of a third time zone. 

Much like the Submariner and the Explorer, the GMT-Master would also find itself linked to the James Bond cinematic canon after a legendary onscreen appearance: actress Honor Blackman, as Pussy Galore, wore it in 1965’s Goldfinger, and her character’s double-entendre name would enjoy an enduring identification with the model as well. 

Best Rolex Watch for the Boardroom:

Rolex Day-Date “President” (1956)

The Rolex Day-Date, introduced in 1956 with Ref. 6510 and 6511, was the first wristwatch that displayed both the date (in the now-familiar 3 o’clock position under the Cyclops lens) and the current day of the week (in a curved window above the Rolex logo at 12 o’clock). The Day-Date’s 36mm gold Oyster case had the fluted bezel emblematic of its stylistic predecessor, the Datejust, and housed the automatic Caliber 1055. Starting in the 1970s, Day-Date watches were outfitted with other mechanical movements that added hacking seconds functionality and quick setting for the day and date, and eventually with quartz movements as part of Rolex’s “OysterQuartz” series of the late 20th Century. In keeping with trends of the early 2000s, Rolex began offering Day-Dates with larger 41mm cases in 2008 (now referred to as the Day-Date II models). Today, the two sizes available are the 36mm version, which carries on the spirit of the original, and the 40mm models, which are aimed at larger wrists but subtly more modest than the 41mm Day-Date II models that were discontinued in 2015; both are equipped with the ultra-modern Rolex automatic Caliber 3255.

The Day-Date is also known as the “President,” a nickname that it began earning as early as the 1960s when President Lyndon B. Johnson wore one regularly in office. The watch also claims a historical, if somewhat scandalous, connection to LBJ’s predecessor, John F. Kennedy, who was purportedly given one as a gift by his mistress, actress Marilyn Monroe. The watch in question, with an inscription in its caseback reading, “Jack, with love as always from Marilyn, May 29th, 1962,” was sold at auction in 2005 to an anonymous bidder. In addition to its association with heads of state, the “President” has become a luxury badge for powerful people real and fictional: actor James Gandolfini famously sported a gold Day-Date in his role as mob chieftain Tony Soprano on the HBO series “The Sopranos.” The sturdy three-link bracelet that made its debut on the original Day-Date also bears the nickname “President” and remains reserved for Day-Date models and for certain ladies’ Datejust models.

Best Rolex Watch for Science Nerds:

Rolex Milgauss (1956)

Diving and air travel were not the only pursuits that were becoming more common in the 1950s; another, for better or worse, were occupations that exposed professional people, such as scientists and technicians, to strong magnetic fields on a regular basis. As anyone who’s owned a mechanical watch knows, magnetism is the arch-enemy of a watch’s ability to run reliably and accurately. In 1956, Rolex took on the challenge of making a watch that could be counted on in high-magnetism situations with the release of the first Milgauss, whose signature innovation was a miniature magnetic shield called a “Faraday cage,” made of ferromagnetic material and placed inside the case to guard the movement from the ill effects of magnetic fields. Its name was a contraction of “mille gauss” — mille being “1,000” in French, gauss being the international unit of measure for magnetic field strength, named for German physicist Carl Gauss — which signified the watch’s unprecedented level of magnetic resistance. Appropriately, the Rolex Milgauss became popular among scientists of the Atomic Age, including those working at Switzerland’s European Organization for Nuclear Research (CERN), which had worked with Rolex to develop the watch. The original Milgauss (Ref. 6451, above) resembled the Submariner but was distinguished by its honeycomb-pattern dial and lightning-bolt seconds hand. 

In the modern era, we are all more surrounded by magnetic fields than ever before, from microwave ovens, cell phones, et cetera, which may have prompted Rolex to re-release the Milgauss in 2007. The new model includes an orange seconds hand, whose lightning bolt shape calls to mind the original model and its retro-futuristic design. The case is made of 904L stainless steel, a surgical-grade alloy that Rolex has long referred to as “OysterSteel,” measuring 40mm and resisting water to 100 meters. The modern movement, Caliber 3131, resists magnetism even more than its predecessor, not only guarded by the ferromagnetic inner case but also equipped with components made from antimagnetic materials, like the patented blue Parachrom hairspring and nickel-phosphorus-alloy escape wheel. 

Best Rolex Watch for a Road Trip:

Rolex Cosmograph Daytona (1963)

Rolex had established a connection to motorsports and auto racing early in its history: British racing driver Sir Malcolm Campbell wore Rolexes on and off the track during his storied career, including in 1935 when he set a world speed record in his famous Campbell-Railton Bluebird at Florida’s Daytona Beach. Daytona, of course, eventually began playing regular host to automobile racing, and in 1959, with the building of the Daytona International Speedway, it inaugurated the annual running of the Daytona 500 stock car race, now a fixture on the American motorsport calendar. In 1962, Rolex became official timekeeper of the Daytona 500, and one year later it released the Ref. 6239 Cosmograph, nicknamed the “Daytona” (though the name had yet to appear on the dial), its now-famous racing-inspired chronograph watch. The watch was notable for its three-register dial and engraved tachymeter bezel. 

Rolex had dabbled in wristwatch chronographs previously, in the 1950s, with similar looks but none of these “pre-Daytonas” generated the mass appeal of Ref. 6239, and part of the reason for that was the star power bestowed upon it by its most famous wearer, actor Paul Newman, who embarked upon a successful second career as a racing driver after starring in the 1969 movie Winning. The model he wore, and which is now nicknamed for him, is one of the rarest collectible timepieces on the secondary market, with an off-white-and-black “panda” dial layout, square-tipped hashmarks and Art Deco-style numerals; the Daytona actually owned by Newman fetched a record $17.8 million at auction in 2017, making it one of the most expensive watches ever sold. 

Like a high-performance race car upgrading to faster and more powerful engines, the Rolex Daytona continued throughout its decades on the market to stay on the cutting edge of chronographic excellence. The original Valjoux movement in the original references eventually gave way to the Rolex Caliber 4030, a heavily modified version of Zenith’s legendary high-frequency El Primero movement (you can learn more about it here) in the late 1980s. That movement was superseded by the in-house Rolex Caliber 4130, with a column-wheel chronograph mechanism and a host of Rolex-patented technical details including a hairspring made of blue Parachrom, an antimagnetic alloy. A personalized, steel-and-gold Rolex Daytona (like the one above) is still awarded to winning drivers of all the races Rolex sponsors, including the Daytona 500 and the 24 Hours of Le Mans. As demand for new Daytonas through traditional retail channels increasingly exceeds supply, a cynic might even say that winning a race is the easiest way to get one.

Best Rolex Watch for a Day of Sailing:

Rolex Yacht-Master (1992)/Yacht-Master II (2007)

It was nearly three decades after the debut of the Daytona before Rolex introduced a new model to its Oyster Perpetual collection of sport-luxury timepieces. That watch was the original Yacht-Master, launched in 1992, the foundation of the only Rolex watch family to emerge from the 1990s. Initially only offered in yellow gold (Ref. 16628, above), the Yacht-Master was visually similar in many regards to the Submariner, with the same geometric hour markers, Mercedes hands, screw-down crown, and Oyster-style case and bracelet. Its rotating bezel was executed more luxuriously, in the same gold as the case and bracelet with a relief-engraved scale, which signified this nautically inspired model as more upscale than the sportier dive watch that it emulated. Other models followed throughout the ‘90s and 2000s, including steel-and-gold “Rolesor” editions as well as the rarer and more exclusive “Rolesium” models, which melded steel with platinum. Their solid metal bezels with 60-minute relief-engraved scales were the primary aesthetic element distinguishing them from the Submariner family, whose bezel inserts are generally smooth.

The Yacht-Master is probably most notable for combining several firsts for the brand in 2015. The Ref. 116655 was the first Yacht-Master in Rolex’s proprietary rose-gold alloy called Everose gold. Its bezel was executed in black Cerachrom, which as its name might suggest is the company’s own extra-hard, corrosion-resistant ceramic material. And it was the first watch to be mounted on Rolex’s innovative Oysterflex bracelet (as on the model above), which on its exterior resembles a fairly traditional black rubber strap but on its interior is equipped with a patented “longitudinal cushion” system, made up of nickel-titanium blades inside an elastomer coating, which gives it the suppleness and comfort of a strap and the robustness and stability of a bracelet. As with other models, particularly the Explorer, Rolex rolled out a distinctly more horologically complex version of the Yacht-Master in 2007: the Yacht-Master II features an additional regatta countdown function that is particularly useful for anyone wearing the watch for actual yacht racing. The original Yacht-Master, which featured 40mm diameters for most of its precious-metal cases, got a big brother in 2019: Ref. 226659, whose new, white-gold case was expanded to 42mm and which was also released on a black Oysterflex. Like all of the more venerable models spotlighted in this feature, today’s Yacht-Master carries inside it an in-house movement with COSC chronometer certification, the Rolex Caliber 3235, packing a 72-hour power reserve and all the patented technology that Rolex fans have, by now, come to expect and demand.