For a lot of guys, picking out a vintage watch begins and ends with a single brand: Rolex. This isn’t for a lack of worthy alternatives—there are plenty, and we’ll cover them all in these guides—but because there are just so many iconic Rolex models, each groundbreaking in its own way. From the original waterproof Oyster, to the Explorer that accompanied Sir Edmund Hillary up Mount Everest, to the Submariner, 007’s diving watch of choice in Dr. No, pretty much every Rolex has a cool backstory. And a cool backstory is exactly what you want in a vintage watch. Well that, timeless design, and a track record of appreciating in value—but Rolexes have this, too. Horological expert Ben Clymer, of Hodinkee.com, has the lowdown, from bezel to backstory.

History
The quintessential Swiss brand was actually founded in London by a German named Hans Wilsdorf in the early 1900s. The origin of the name is uncertain, but the two leading theories are that it is an amalgam of horlogerie exquise (exquisite watchmaking), or that “Rolex” was Wilsdorf’s interpretation of the sound a watch made when it was being wound. Regardless, the name is pronounced the same way in every language, which has served the brand well as it has grown to dominate the global market for mechanical watches. 

Wilsdorf moved his company from London to Geneva in 1919, and debuted the waterproof Oyster case soon afterward. In 1927, Wilsdorf engineered what many believe to be the first example of product placement, equipping English typist Mercedes Gleitze with an Oyster to wear during her second swim across the English Channel in 1927. Gleitze’s attempt failed, but—more important for Wilsdorf’s purposes—the watch worked beautifully.

In subsequent decades, Rolex’s connection to high-profile personalities—and world firsts in science and exploration—bolstered the brand’s reputation for innovation and durability. In 1953 Sir Edmund Hillary wore an early example of the Explorer to the summit of Mt. Everest, and in 1960 a special Rolex diving watch named the Deep Sea joined Jacques Piccard and Don Walsh aboard the Bathyscape Trieste when it dove to the Mariana Trench, the deepest point in the ocean. The GMT-Master, the first watch with a fourth hand (for a second time zone), was codeveloped with Pan-Am and issued to its pilots for decades. Through the '60s and ’70s, the Submariner, considered by many to be the most revered watch ever built, adorned the wrists of British frogmen, divers for French offshore drilling company Comex—and, of course, the wrist of Sean Connery in the first James Bond movie, Dr. No.

By the early ’70s, with the advent of quartz watches, mechanical watches were suddenly out of favor. It may seem hard to believe now, but for a while, battery-powered quartz watches were generally more expensive, and were considered far more prestigious. The trend was short-lived, however, as battery-powered quartz watches became commonplace, and mechanical movements were seen as a luxury rather than necessity. With the proliferation of digital technology, that trend has only intensified, and now a vintage Rolex can feel like a tactile antidote to the proliferation of touchscreens.

Models to Know
Rolex makes a small number of models, but they’re all icons. Divided into “sport” and “non-sport” categories, most of them employ the waterproof Oyster case, Rolex's properitary waterproof design that inspired the entire industry to look at water resistance as a necessary feature of mechanical watch cases. In the sport category, the principal models are the Submariner, Daytona, GMT-Master, Explorer, and Explorer II.  In the non-sport category, the key models are the Day-Date and the Datejust.   

Notable Rolex Fans

Paul Newman
The actor, philanthropist, and all-around awesome guy had an exotic-dial Daytona named after him. He was seen wearing five different Daytonas throughout his lifetime.

Steve McQueen
McQueen had an Explorer II named after him—though in recent years, it’s come to light that he never owned this watch (he wore an early Submariner, and now the 5512 is known as the McQueen Submariner). 

Jean-Claude Killy
The French Olympian has a model named after him as well, the reference 6236 Dato-Compax. Killy, a known vintage collector, is a member of Rolex’s board.

Robert Redford
Redford has been wearing the same red Submariner, reference 1680, for decades. It can be seen in several of his films (The Candidate, All the President’s Men).

Brad Pitt
Pitt is a long-time Rolex fan and has been seen wearing Submariners, Daytonas, and Day-Dates. 

Harry Truman
Truman, one of the many presidents to wear the Crown (usually after leaving office), wore an early example of the Datejust for many years. 

John F. Kennedy
Though JFK wore an Omega for his Inauguration, he was supposedly gifted a Day-Date by Marilyn Monroe for his birthday in 1962. She signed the case back—but out of respect to the first lady, he never wore the watch. It sold at auction in 2005 for $120,000. It’s a real Rolex—but many experts doubt its provenance.

Warren Buffett
Buffett, known for living well below his means, has been spotted wearing a Day-Date in yellow gold.

Eric Clapton
An avid watch collector, Clapton has owned several rare Rolexes, like an “albino” Daytona, an Explorer Dial Submariner, and several early chronographs dating to the ’40s.

John Mayer
Mayer picked up where Clapton left off, and is now known as one of the biggest collectors. He is particularly keen on Paul Newman Daytonas.

Click the link below to learn more about each key Rolex model, starting with the Submariner.