The Beginner’s Guide to Rolex Watches for Men

Over a century after they first hit the market, Rolex watches for men still set the standard. It’s hard to explain just how dominant Rolex is in the watch space, and even the most breathless analogies tend to fall short. If you know nothing about watches, you’ve probably heard of Rolex; if you know anything about watches, you probably want a Rolex. And if you know a lot about watches, you probably already own one—or are obsessively eyeing the gray market waiting for your moment to pull the trigger. 

Rolex’s enduring appeal comes down to a savvy mix of heritage, marketing, craftsmanship, and collectibility. Since 1905, the Swiss brand has worked tirelessly to solidify its status as one of the world’s most innovative watchmakers, pioneering the water-resistant case, the self-winding movement, the day-date display, the ultra-deep dive watch, and the rainbow bezel. That the watches themselves are top-of-the-line in every way almost goes without saying—which says a lot in and of itself. Their movements adhere to Rolex’s exacting standards for accuracy; every element is obsessively considered and incessantly improved upon.

Despite the brand’s commitment to innovation, though, Rolex isn’t known for making big changes to its products. While other brands release a slew of new models throughout the year, Rolex can generate the same amount of hype by adjusting a case size by a millimeter and offering a single new dial color. Its current catalog consists of only about a dozen models, but among them are some of the most iconic designs of all time, including the Submariner (the gold standard in dive watches), the Daytona (the world’s most coveted chronograph), and the Day-Date (a perennial go-to of enlightened high-rollers like Rihanna and the Dalai Lama).

So it might come as a surprise to any wide-eyed watch newbs to hear that you can’t just stroll into your local jewelry store and buy your Rolex of choice, even with a suitcase full of cash. Depending on which model you want, you may have to wait weeks, months, or even years to snag your grail from an authorized dealer—and that’s to say nothing of Rolex’s secret menu of tickers, which are only available in limited numbers to select buyers at the discretion of the dealer.

For anyone who doesn’t want to wait, countless gray market sellers will gladly charge you a hefty premium for a new or “nearly-new” Submariner, and the vintage market is chock-full of Rolex grails from decades past. So if you’re in the market for a Rolex (and if you’re still reading this, you probably are) here’s a rundown of everything in the crown’s current lineup—the most covetable Rolex watches for men on the market right now—to whet your appetite.

The Rolex Submariner

Every genre has its GOAT, and when it comes to dive watches nothing comes close to the iconic Submariner. The Sub was the first watch rated waterproof to 100 m, and it led the way in style and performance ever since its debut in 1953. Every element of the Submariner’s design has been dictated by its origins as an elite diver’s tool watch, from its unidirectional rotating bezel (used to time dives and decompression) to its Oyster bracelet with the Glidelock extension system (for when you need to wear it over a wetsuit). Now rated to 300 m below the waves, and made from Oystersteel, Rolex’s proprietary stainless alloy, along with gold, and two-tone variants, the modern Sub is still the benchmark against which all other divers are measured.

The Rolex GMT-Master II

Rolex designed the original GMT-Master for Pan Am airline pilots in the 1950s, simultaneously creating the template for the modern travel watch and one of the most coveted accessories of all time. The GMT-Master II’s defining characteristic is its bidirectional rotatable bezel available in a range of two-tone combinations, which distinguish night from day and allows pilots to track their flights over multiple time zones with a glance. Thanks to a bevy of color combinations with clever nicknames like “Batman” (black and blue), “Sprite” (green and black) and the OG red and blue “Pepsi,” the GMT-Master II is a certified flex at any altitude.

The Rolex Cosmograph Daytona

If you got into watches anytime after 2017, the Rolex Daytona probably had something to do with it. That was the year a Daytona once owned by Paul Newman sold for nearly $18 million—setting the vintage watch market on fire in the process. Designed in the 1960s to time laps at the Daytona International Speedway in Florida (and still given to winners of the Rolex 24 at Daytona race each January), the Daytona has become one of the most collectible watches on the planet. To celebrate the model’s 60th birthday this year, Rolex overhauled the entire Daytona line with a new chronograph movement, adding a sapphire case back to the platinum version, and rolling out a new model in white gold with a vintage-inspired dial.

The Rolex Yacht-Master

As sports go, yachting is up there with polo and fencing when it comes inaccessibility and general abstruseness—which might explain why the Yacht-Master doesn’t get as much attention as some of its siblings. You don’t, however, need a yacht club membership or a working knowledge of how to raise a spinnaker to appreciate its charms. It’s the only “Professional” Rolex model available in three case sizes (37mm, 40mm, and 42mm), and while its bezel, dial, and Cyclops date window give it a similar look to the Submariner, the Yacht-Master scores points for originality as one of two Rolex models available in the brand’s proprietary RLX titanium.

The Rolex Yacht-Master II

In 2007, 15 years after introducing the Yacht-Master, Rolex took its sailing watch to the next level by adding one of the most complicated movements the brand has ever made. Equipped with a programmable countdown and a mechanical memory, the Yacht-Master II is designed to help yachtsmen time the start of their regattas with Swiss precision, not to mention look great with a double-breasted navy blazer.

The Rolex Sea-Dweller

Ever since inventing the waterproof case back in the 1920s, Rolex has been creating watches equipped to push ever-deeper into the abyss. The Sea-Dweller launched in 1967 with an impressive water-resistance rating of 610 m, and has since doubled that to an even more audacious 1220 m. Burlier and heavier than the Submariner, the Sea-Dweller is as much a proof-of-concept as it is a beefy fashion accessory.

The Rolex Deepsea

Rolex took another big plunge in 2008 with the launch of the Deepsea, a.k.a. the watch worn by James Cameron when he ventured seven miles below the ocean’s surface to the Mariana Trench. If you’re headed down that way, or just find the Sea-Dweller’s 1220 m of water-resistance too paltry, this watch’s 3900 m water-resistance rating (and distinctive “D-blue” gradient dial) should do the job nicely.

The Rolex Deepsea Challenge

Some watches are made to be worn, and others are made to prove a point. The Rolex Deepsea Challenge, which is rated water-resistant to 11,000 m (which, not incidentally, is deeper than the deepest part of the ocean), is very much the second kind. Despite being made out of ultralight RLX titanium, the Deepsea Challenge’s 50 mm wide and 23 mm thick case pushes the limits of wearability, a small price to pay for ultimate bragging rights.

The Rolex Air-King

The Air-King doesn’t command as much clout as some of the other aviation watches in the Rolex family, but it might be the most underrated of them all. It doesn’t have the GMT-Master’s colorful bezel or the Sky-Dweller’s complicated movement. What it does have, though, is one of the more unusual dials of the bunch, complete with a prominent minute scale (a nod to its roots as a pilot’s navigation tool), a Rolex-green seconds hand, and the distinction of being far less ubiquitous than other pieces in the crown’s Professional watch lineup.

The Rolex Explorer and Explorer II

This unassuming Rolex traces its history back to the 1950s, when Tenzing Norgay and Edmund Hillary became the first people to set foot on the summit of Mount Everest. Rolex supplied the mountaineers with a watch that would later become the Explorer, a sturdy, no-nonsense ticker made to stand up to the harshest conditions on the planet. The modern Explorer’s signature feature is its unusual 3-6-9 dial (also known as an Explorer dial) and a choice of 36 mm and 40 mm case sizes in Oystersteel, or two-tone Oystersteel, and yellow gold. The Explorer II, which arrived in 1971, is larger at 42 mm and more technical, with a GMT hand and 24-hour bezel to help explorers (and anyone else who frequently hops time zones) track multiple times at a glance.

The Rolex Oyster Perpetual

Among Rolex’s biggest flexes as a watchmaker is the fact it invented the first waterproof wristwatch, the Oyster, back in 1926. The Oyster Perpetual—a family of simple-yet-versatile sports watches with sturdy Oystersteel cases and a selection of colorful dials—is the descendent of that 1920s trailblazer. Despite being the most modestly-priced member of the Rolex family, elements like the Oyster bracelet and a Superlative Chronometer-certified automatic movement make the Oyster Perpetual every bit worthy of the Rolex name. The OP also comes in more case sizes than any other Rolex model, ranging from 28mm to 41mm, with dials in shades of navy, green, champagne and—most coveted of them all—don’t-call-it-Tiffany turquoise. The hottest new OP variant of 2023 features a “Celebration motif” dial of multicolored balloons that’s tailor-made to attract attention on red carpets and in NBA tunnels across the country.

The Rolex Datejust

With classic Rolex design elements like a fluted bezel, jubilee bracelet, and “Cyclops” magnifying lens over the date window, the Datejust is as close to a Platonic ideal Rolex as it gets. The Datejust collection has been around since the 1940s, and now spans dozens of models in Oystersteel, two-tone Oystersteel and gold, along with three kinds of pure gold (yellow, white, and Everose. It comes in three case sizes, too, with three bracelet options, a choice of fluted, domed, or gem-set bezels, and a whole whack of dials. And lest anyone think Rolex doesn’t know how to have fun, the brand shook things up in 2021 with the addition of patterned dials in palm leaf and fluted motifs.

The Rolex Day-Date

When Rolex debuted a Day-Date 36 with a rainbow puzzle dial and a selection of emojis in place of the date, it nearly broke the internet. (Or, at least, a very narrow slice of it.) That model, sadly, is off-menu and highly limited, but it’s just one of many Day-Dates vying for a spot on wrists around the world. First introduced in 1954, the Day-Date’s claim to fame then, as now, was the day of the week spelled out in an arc across the top of the dial. Making the day and date click over precisely at the stroke of midnight was a technical feat in the ‘50s, and it helped the Day-Date earn a place on the wrists of bigshots like JFK, Fidel Castro, and Jack Nicklaus—and the nickname ‘the President’s watch.’ Today’s Day-Date comes in dozens of variations in 36mm and 41mm case sizes, and in line with its high-rolling rep, it’s available exclusively in gold or platinum. If you’re looking for a Day-Date with a little extra clout, check out the 36mm models with dials made of turquoise, aventurine, and other colorful semi-precious stones.

The Rolex Sky-Dweller

If there was such a thing as an underrated Rolex it would be the Sky-Dweller, which also happens to be one of the most complicated watches in the brand’s current lineup. Released in 2012, the Sky-Dweller offers dual time zones, a “Saros” annual calendar, and Rolex’s much-ballyhooed Ring Command system, which (if you’re into watch complications) is absolutely as cool as it sounds. Dual-time watches and annual calendars can be notoriously fussy when it comes to setting the date and time, but the Sky-Dweller’s ingenious design makes the process relatively simple: by rotating the fluted bezel in combination with the winding crown, you can easily adjust the reference time, local time, and date when you touch down in a new zone. For 2023, Rolex added an upgraded movement and new dial options in green and green-blue into the mix, which ought to earn the slept-on Sky-Dweller some well-deserved attention.

The Rolex 1908

In 2023, Rolex discontinued the Cellini, the dressiest member of the Rolex squad, and replaced it with the 1908, the brand’s first all-new model in more than a decade. (The 1908 is also the first member of Rolex’s new heritage-themed family of watches, the Perpetual collection.) Named for the year that founder Hans Wilsdorf registered the Rolex name in Switzerland, the 1908 is a tribute to old-school watchmaking with a classic petite seconde layout featuring a second subdial at six o’clock. Like the Cellini before it, the 1908 is all about classic elegance, with refined details like a 39mm gold case, a fluted-and-domed bezel, and an alligator leather strap. The coolest thing about the 1908, though, might also be the least obvious: a sapphire case back offering a view of the automatic movement inside. Display case backs are pretty common these days, but very few Rolexes incorporate the detail, making it a Roger-Federer-at-the-Met-Gala-level flex.