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The Best Rolexes for Men Based on Your Lifestyle

Image courtesy of The Creative Image courtesy of The Creative

President Joe Biden caused a media stir when he was spotted wearing a $7,000 Rolex watch at his inauguration. How dare he flaunt such an icon of status? Turns out, of course, that Biden knows quality watches, owning a selection of Rolexes and Omegas; and that he joins a presidential tradition of wearing the iconic brand extending back at least as far as the Eisenhower era. 

Rolex is a Swiss company that is probably the most recognized watch brand in the world. In 1905 founder Hans Wilsdorf dreamed of making a reliable wristwatch (most people still wore pocket watches at the time), and with the invention of the world’s first waterproof watch in 1926, Rolex went on to become the choice of explorers and adventurers the world over. Wilsdorf called his innovation the “Oyster,” because its system of screwing down the bezel, case back, and winding crown against the middle case ensured that the case was hermetically sealed and protected. Since then the brand’s fare has become the stuff of legend, a blue-chip investment that’s right up there with good real estate. 

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In January 2020, a guest on PBS’s Antiques Roadshow was an Air Force vet who’d been stationed in Thailand in the mid-1970s. A scuba-diving enthusiast, he’d ordered a Rolex Oyster Cosmograph  through his base exchange. Once he got it, he decided it was too nice to wear, so he tucked it into a safe deposit box for 45 years. At the time he’d spent $350 — about a month’s salary — on the timepiece: on the show it was estimated to be worth between $500,000 and $700,000 dollars. 

Ready to make your own investment in time? Beyond this list of our favorite watches, here are our selects from the Rolex range to consider; from some that (might be) about a month of your salary, up to more extravagant editions that may come your way with some luck, hard work, or maybe inheriting a trust fund or two. Check out the Rolex store locator for a certified retailer near you, or head to Chrono24, an online marketplace for luxury watches. Not quite ready to make that kind of a commitment? Consider some of these lovely alternatives, watches for less than $500.

Best Starter Rolex: the Oyster Perpetual 41

That promotion turned out to be even bigger than you thought, so it’s time to show you’re ready to play with the big dogs, and choosing this Rolex shows you know a good investment when you see one. The brand’s signature “sunray” dial is clean and minimal (available in several hues, but we prefer this classic silver), perfect paired with the “Oystersteel” corrosion-resistant steel case, and the Oyster bracelet. It’s perfect to wear with every suit you own, but will look just as dazzling with denim. 

Best for the Frequent Flyer: the Air King Oyster

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Whether you just earned your pilot’s license, just built up more miles than a flight attendant, or just plain have your head in the clouds; Rolex’s Air King is just for you. Designed in the 1950s to celebrate the Oyster’s aeronautical heritage, it features  a combination of large 3, 6, and 9 numerals marking the hours and a prominent minute scale for navigational time readings. Similar to the Perpetual in style, the face is slightly sportier, and may favor your office casual wardrobe. 

Best for the Geek: the Milgauss Oyster

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If wearing a white lab coat and safety glasses is your idea of sartorial perfection, the Milgauss is the only accessory you need (maybe a pocket protector for your Montblanc?). It’s also the watch  to own if you’re accident-prone: the Rolex-developed green sapphire crystal is scratchproof and fade-proof, with an alchemical light green shade that fairly glows at the edges. We recommend the electric blue dial to complement the crystal’s jade hue while offsetting the orange lightning-bolt-shaped seconds hand. A true scientific wonder, it’s called the Milgauss because it can withstand magnetic fields of up to 1,000 (“mille” in French) gauss.

Best for the Deep Sea Diver: the Submariner Date 

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Whether you’re Jacques Cousteau’s heir apparent or just like to splash around in the pool with the kids, the Submariner provides features designed for the depths, and of course that reliable Rolex waterproof seal. The rotatable bezel has 60-minute graduations to accurately and safely monitor diving time and decompression stops. A hard, corrosion-resistant ceramic bezel insert is virtually scratchproof, and a luminescent capsule on the zero marker and Chromalight display ensures legibility no matter how dark the environment (attributes that are pretty handy even when topside). The bezel’s knurled edge offers excellent grip under water, even with gloves. 

Best for the Traveler: the GMT-Master II

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If you’re an inveterate traveler — or just the guy who’s been tasked with keeping an eye on the company’s overseas accounts — you’ll appreciate this Rolex for its ability to track two time zones. Beyond the hour, minute, and second hands, an additional arrow-tipped hand circles the dial once every 24 hours, while the ceramic bezel can be rotated to display an alternative time zone or a reference time. We particularly like this Everose gold model for its elegant ostentation, the perfect thing to catch the attention of that first class cabin flight attendant. 

Best for the Romantic: the Cellini Moonphase

If you insist on wearing a boater with your seersucker suit, and you binge-watched Bridgerton, Rolex has something for you, too. Named for a Renaissance artist, the Cellini series combines all of the brand’s superior engineering with heritage focused design. In this model the lunar cycle is clearly displayed at the bottom of a white lacquer dial (Hmm. Maybe this is a good choice for werewolves?) The retro look is completed with a fine leather watchband. 

Best for the Racer: the Cosmograph Daytona

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How many speeding tickets can one man rack up? No judgments here. We’ve all been there: The open road and a spirited automobile is an invitation to push our limits. Rolex understands and designed the Cosmograph Daytona for the budding race car driver in all of us. The bezel features a tachymetric scale for measuring average speeds of up to 400 mph, as well as precise chronograph dials. The black Oysterflex bracelet is a super-elastic metal blade “overmoulded” with high-performance black elastomer. 

Read more: Best Automotive-Inspired Watches

Best for the Connoisseur: the Day-Date 40

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Life’s too short to … We’ll let you fill in the blank. You only drink Krug, and you’ll put your Benz up against anybody else’s wheels any day. Platinum describes so many things in your life, but at Rolex, it’s used to update and ennoble one of the brand’s most practical models, a favorite since its debut in 1956. The Day-Date was the first watch to show the day of the week, spelled out on the face of the watch. Customize yours to include your language of choice. 

Best for the Seafarer: the Yacht-Master II

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It’s not a boat. It’s not even a ship. Your yacht is both your pleasure and your passion, and when aboard you want to maintain the competitive style that tradition demands. With the Yacht-Master II, you’ll already be way ahead of the competition. This Rolex is the only chronograph in the world with a mechanical memory: The bezel operates in conjunction with the internal mechanism, allowing it to be set and synchronized to the sequence of race start times. We’re particularly fond of the nautically inspired styling of this yellow gold and marine model. 

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John Jones
John Jones is a Jersey City, New Jersey-based writer who enjoys covering design in all its forms, from fashion to…
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