If you need to tell time, well, there’s a mobile phone in your pocket that can help. If, however, you need to communicate something about who you are and what you hope to accomplish in this life, that’s where a watch comes in. (Bonus: It also tells time.)

A watch is essentially jewelry with a purpose—a wedding of form and function that’s equal parts decorative and meaningful. It can be an accent piece you throw on to complement a suit. It can be a deeply meaningful talisman you intend to pass along some day to your son. And it can be all or none of the above. But no matter what your intent is, one thing’s certain: Purchasing a classic men’s watch is a surefire way to ensure your investment is well spent, whether that investment is in the five figures or is less than a c-note.

Below are 18 iconic watches to consider, including chronographs (stopwatches), dive watches (for underwater diving with some degree of water resistance), dress watches, digital watches, and sports watches (shock-proof and scratch-resistant).

1.Rolex Submariner

Style: Dive watch

Rolex Submariner

Rolexes have adorned the famous wrists of Paul Newman (whose iconic Rolex Daytona sold at auction for a record $17.8 million in 2017) and James Bond, who sported a Submariner for his screen debut in Dr. No in 1962. The dive watch has been a staple for men since 1953, when it became the first wristwatch to be waterproof up to 100m. It bears large, easy-to-read numerals (helpful when you’re underwater), luminescent hour markers and Rolex’s trademark Oyster case (which dates to the first-ever waterproof watch, from 1926). And while vintage Rolexes hold their value extremely well, we can’t guarantee yours will go for nearly $18 mil.

Price: $7,050

2.Omega Speedmaster

Style: Chronograph

Omega Speedmaster

For the astronauts landing on the moon, the Speedmaster was an essential tool—a tricked-out timepiece with three sub-dials (set to measure 60 seconds, 30 minutes and 12 hours), a tachymeter (which measures travel time, or distance based on speed) and an ultra-precise hand-wound movement. Introduced in 1957, the Speedmaster gained iconic status 50 years ago when Buzz Aldrin wore it on the surface of the moon. It remains an icon due to its seamless blend of high functionality with elegant design. A smart pick even if your workplace is of the terrestrial variety.

Price: $5,350 (for Moonwatch version)

3.Breitling Navitimer

Style: Chronograph / Aviation

Breitling Navitimer

For more than six decades, Breitling has been synonymous with aviation. Its signature Navitimer series was designed with pilots in mind—the design inspired by an airplane’s gauges, and the brand famously included a slide rule on each case to assist pilots with their calculations. Recently, the brand has refreshed the line with both collaborations (Pan Am and TWA models) and the Navitimer 8 line, which boasts a slimmer silhouette and a more accessible price point.

Price: Navitimer 1, $5,820; Navitimer 8, $3,980

4.Cartier Santos

Style: Dress watch

Cartier Santos

Cartier didn’t invent the wristwatch, but the Santos was the first one to become popular with men, thanks to its daring namesake: Alberto Santos-Dumont, a Brazilian pilot who asked his buddy Louis Cartier to design a timepiece that wouldn’t require him to take his hands off the controls of his plane. This is the result, and it’s been a definitive dress watch for more than a century (as has Cartier’s Tank, which features an elongated rectangular case, as opposed to Santos’ squarer original). The brand relaunched the Santos in 2018, meaning you no longer need to pony up for a vintage model (or suss out whether it’s the real thing).

Price: $6,250

5.TAG Heuer Monaco

Style: Chronograph

TAG Heuer Monaco

No actor is as synonymous with speed and style as Steve McQueen, and so it is with this timepiece, which he wore in his legendary driving film, Le Mans, in 1970. But this watch can claim more than just celluloid glory—it was the first square-shaped waterproof watch, and the first automatic chronograph (meaning you don’t have to wind it). TAG’s famed for pushing the boundaries—it was on John Glenn’s wrist when he became the first man in space, and TAG stands for Techniques d’Avant Garde. Wearing one shows the world that you think outside the box, even if your watch resembles one. Oh, and a pro tip: It’s pronounced tagh-HOY-er.

Price: $1,750

6.Breguet Classique

Style: Various

Breguet Classique

This storied French brand has been producing elegant timepieces for three centuries and counting, and can count Marie Antoinette and Winston Churchill among its fans. Its Classique line encompasses a range of offerings, each of which can be worn in a dressy setting. We’re partial to the 5140, a streamlined piece that showcases Breguet’s signature moon-tip hands (a staple since around the time of the American Revolution), Roman numerals and a self-winding mechanism.

Price: $19,900

7.Casio G-Shock

Style: Digital watch

Casio G-Shock

The pioneering digital watch remains an icon, as definitive of the ‘80s as the Royal Oak is to the ‘70s. The original design was inspired by car tires and caterpillars, a funky bit of nerd-chic that still charms in the era of Apple Watches and Fitbits. Casio has expanded the line to include non-digital versions, as well as smart iterations, but nothing matches the analog beauty of the original.

Price: $99

8.Grand Seiko Spring Drive

Style: Sport watch

Grand Seiko Spring Drive

If you’re looking to impress insiders—or just up your Instagram game—Grand Seiko might be the hottest brand in watchmaking right now. The reason? Restless collectors are looking beyond the traditional hotbeds of watchmaking (mainly Switzerland) to places like Japan, where Grand Seiko plies its trade from a mountain town north of Tokyo. Spring Drive watches are powered by its namesake movement, which pairs traditional mechanical watchmaking with a quartz-powered electronic technology, assembled by hand for a blend of craftsmanship and precision. If you want the beauty and quality of the brands you know and love, but want something a little unexpected for a conversation starter, this is your play.

Price: $5,200

9.Jaeger-LeCoultre Reverso

Style: Dress watch

Jaeger-LeCoultre Reverso

Few timepieces can compare with the elegance of the Reverso, an Art Deco masterpiece with a secret. Originally designed for British polo players in India, the Reverso sports a reversible case that protects the watch’s crystal case while its wearer is on the field. (Hence the name.) Despite its sporty origins, it is more commonly worn as a dress watch today, thanks to its elongated case and those swooping, ‘30s-era numerals.

Price: $4,150

10.Hamilton Khaki Field

Style: Field watch

Hamilton Khaki Field

Hamilton famously supplied the U.S. military with field watches during World War II, and little in the brand’s designs have changed since then. There is nothing fussy about the design—big, easy-to-read numbers, with straightforward hands and a canvas strap. But, much like some of the military’s other notable contributions to civilian life—the field jacket, the Jeep—there is a certain rugged beauty to that simplicity. Of note: The brand now uses high-quality, Swiss-made movements.

Price: $475


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