Tyler, the Creator Just Proved That the Coolest Watch in the Room Isn’t Necessarily the Most Expensive

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The hip-hop world is full of hype watches.

Actually, maybe it’s more accurate to say the hip-hop world creates hype watches. Tyler, the Creator—the American rapper, record producer, actor, and streetwear brand owner—has become a passionate and dedicated watch collector, known especially for his preference for diminutive Cartier pieces that many enthusiasts ignore. (Bangs table and mumbles unintelligible “I told you so” about small watches finally making a comeback.)

This week in LA, Tyler was spotted wearing a vintage Louis Vuitton Monterey II, a watch that’s so left-of-center, it hasn’t taken off on the secondary market rocket ship yet. (And this despite LV’s recent ascendance in the watch world under the direction of Jean Arnault, LVMH scion Bernard Arnault’s youngest son.) It seems possible that the appointment of Tyler’s close friend and hero Pharrell to the head of men’s design at Louis Vuitton could have inspired the new acquisition. The Monterey II, designed by Italian architect and designer Gae Aulenti in 1988, is a unique alarm watch powered by a quartz movement. Housed in a ceramic case, it was produced by the International Watch Company in Schaffhausen, which is famed for its use of innovative materials.

Measuring just 37mm, the watch’s crown is situated at 12 o’clock, while its lugless design necessitates the use of a pull-through strap, which is threaded through the case’s back. Looking like a contemporary fusion of a WWI-era trench watch and something you’d find in the MoMA Design Store, the Monterey II is rarely seen in the wild. They’re also a not-so-common sight on the market where prices vary wildly. They’ve sold on eBay for anywhere between $2,900 and $800 over the last month. Mike Nouveau, the king of watch TikTok/Reels, captured a funny moment recently where a collector offered to pay $4,000 for a version the owner got for only $600 through, he says, a “Japanese auction.” All this makes Tyler’s choice to wear one all the more notable.

If you look at modern LV watches—such as those in the Tambour collection (which itself dates to the early 2000s—you can see a throughline in the design language stretching back to the Monterey series in the 1980s. And given LV’s place in the hip-hop (and greater sartorial) pantheon—and the growing appreciation for its groundbreaking contemporary wares—there’s all the more reason to applaud seeing this small, battery-powered, inexpensive alarm watch on the wrist of a musical tastemaker.

Or, to dramatically misquote Aristotle: “One eye-watering price tag does not a superlative hype watch make.”

Tom Kristensen’s Rolex Daytona “Le Mans”

Danish driver Tom Kristensen has won Le Mans nine times, more than any other competitor in the sacred race’s history. So it was hardly a surprise that when he rolled up to the Rolex Monterey Motorsports Reunion last Saturday, he was rocking the brand new Cosmograph Daytona reference 126529LN, the so-called “Le Mans” Daytona. With its numerous callbacks to various vintage models — “exotic” dial typography, red text, plus a 24-hour totalizer to honor Le Mans—it’s a standout release, and proof that even in retirement, Kristensen remains a winner.

Novak Djokovik’s Hublot Big Bang Unico Magic

One of the world’s best tennis players, Novak Djokovik is no stranger to a great watch—having previously been a brand ambassador for AP and Seiko, he’s seen his fair share of horological heat. Since 2021, however, he’s been part of the Hublot roster, joining fellow athletic icons such as Pelé and Usain Bolt. While hoisting the Rookwood Cup at the Western & Southern Open in Mason, Ohio this week, he was seen wearing a 42mm Big Bang Unico Magic, a ceramic bruiser of a timepiece with a cool transparent dial and a matching, integrated yellow rubber strap. Technical and futuristic, it’s the perfect pairing for the Serbian tennis phenom.

Kyle Kuzma’s De Bethune Kind of Two Jumping GMT

28-year-old Washington Wizards power forward Kyle Kuzma has accumulated quite a collection—one that spans everything from Patek, to F.P. Journe, to Rolex, to Vacheron and more. This week, however, he took a giant leap into the upper strata of haute horlogerie when he was spotted with De Bethune CEO Pierre Jacques sporting one of the brand’s Kind of Two Jumping GMT. An absolutely bonkers feat of horology, this 43.3mm Grade 5 titanium watch features a rotating central case with two dials — one more classically inspired with blued Breguet hands, and one with a gorgeously skeletonized display. Able to display two time zones simultaneously — one on each side — it’s a crown jewel in Kuzma’s already notable collection.

Viktor Hovland’s Audemars Piguet Royal Oak Perpetual Calendar

Norwegian golfer Viktor Hovland sported quite the wrist candy while winning the BMW Championship Cup at Olympia Fields Country Club near Chicago: Strapped securely to his left arm as he hoisted his trophy was an Audemars Piguet Royal Oak Perpetual Calendar Ref. 26579CB.OO.1225CB.01. Executed in white ceramic, this is, in our humble opinion, one of the best-looking perpetual calendars, or quantième perpétuel—and one of the best APs, for that matter—on the market, with indicators for time, day, date, month, leap year, moon phase, and even the week of the year. With its blue “Grand Tapisserie” dial and wildly complicated Calibre 5134 movement, it’s proof that this young golf prodigy has a great eye for watches to match a formidable swing.