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.

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1999 Rolex Explorer Watch

Rolex

1987 Rolex Explorer II Polar Transitional Watch

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 a “Celebration motif” dial consisting of multicolored balloons.

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Rolex Oyster Perpetual 26 Steel Watch

Rolex

Rolex Oyster Perpetual 41 “Tiffany” Turquoise Watch

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 18k 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.

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Rolex Datejust 36 Two-Tone Diamond-Set Watch

Rolex

Rolex Datejust 36 Diamond-Set Silver Watch

The Rolex Day-Date

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. And if you’re after something truly unique (and have the budget to afford it) you can try your luck at tracking down the infamous “puzzle dial” Day-Date, an ultra-limited production model introduced in 2023.

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2023 Rolex Day-Date 40 Yellow Gold Baguette Diamond-Set Watch

Rolex

2017 Rolex Day-Date 40 White Gold Baguette Diamond-Set Watch

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 the most complicated watch 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.

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2021 Rolex Sky-Dweller Yellow Gold Watch

Rolex

2023 Rolex Sky-Dweller 42 Steel Watch

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.

Rolex

2024 Rolex Perpetual 1908 Yellow Gold Watch

Rolex

Rolex Perpetual 1908 White Gold Watch

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