Jay-Z’s Patek Philippe collection is filled with so many gems—proverbial and literal—that it can be difficult to keep track of them all.

But the watch that Hov wore courtside to a Lakers vs. Clippers game this past week is easily a standout. For serious watch guys, there’s its Tiffany stamp and its annual calendar feature—a complication developed by Patek Philippe itself as a simpler version of the perpetual calendar. And for those who crave a bit of bling, there are the bezel, which is set with 36 baguette-cut diamonds, and the gold-over clasp, which has another 22 stones. (Total carat weight: 4.45 carats.) And for those who simply love a beautiful object? Well, the reference 5961R is 40.5mm of pure rose gold, with a black opaline dial arranged in one of the maison’s most beautiful designs. What’s not to like, exactly?

JayZ attends a basketball game between the Los Angeles Clippers and the Los Angeles Lakers

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To be fair, Jay-Z owns more complicated watches and more expensive watches. (Not that the 5961R, which features both an annual calendar and a chronograph complication, isn’t expensive at $161,430. The Grandmaster Chime, however, will set you back a cool $2M.) But for whatever reason, the 5961R, sitting as it does at the confluence of haute horlogerie and precious materials, manages to cram an outsized amount of features and bling without feeling…well, blingy. Maybe it’s the baguette cut of the diamonds, which helps them circle the bezel with a higher degree of subtlety than round-cut stones. Or maybe it’s the rose gold, which flies under the radar better than its yellow-hued compatriot—or maybe it’s the soft, black dial. But the 5961R just feels—at least on Jay’s wrist—like it can work in any setting.

To wit: the man paired it with a black sweatshirt and Air Jordans while courtside at a Lakers game. And while this is certainly the type of watch that, despite its busy, complicated dial, could be worn in 2024 with black tie to an awards show, we’re also seeing a larger trend of dressier pieces worn in everyday settings.

Speaking of that dial, let’s examine what’s going on here: The annual calendar was developed by Patek and debuted in the ref. 5035 in 1996. A stripped-back perpetual calendar, it can keep track of month’s of different lengths throughout the year, and only needs to be adjusted once at the end of February. But the maison didn’t stop there: The ref. 5961 combines this complication with a flyback chronograph, streamlining the displays via a combined 12-hour and 60-minute counter at 6 o’clock, plus day, date, and month counters arranged in an arc at the top of the dial. Somehow, a metric ton of information is displayed in a way that’s easily scannable—and even beautiful.

Powered by one of the brand’s in-house movements, the automatic Calibre Caliber CH 28‑520 IRM QA 24H, the 5961R is a horological work of art, and easily one of the coolest watches in Mr. Carter’s collection.

Odell Beckham Jr. attends the game between the Los Angeles Lakers and the Phoenix Suns

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Odell Beckham Jr.’s Audemars Piguet Royal Oak Perpetual Calendar

Spotted courtside at a Lakers game, Odell Beckham Jr. wore one of the coolest iterations of the Audemars Piguet Royal Oak: The ref. 26579CS Perpetual Calendar. Housed in a blue ceramic case with a matching, integrated bracelet, it features a beautiful blue Grand Tapisserie dial with time, day, date, month, moonphase, and leap year indicators. What makes a perpetual calendar so special—and so expensive—is that it’s “programmed” to remember the different lengths of each month, and thus requires almost no manual adjustment so long as it’s kept wound. Water resistant to 20m, this isn’t a watch that you’d want to beat up—but that’s not really it’s raison d’être. (The point is to be seen in one at a Lakers game.)

James Marsden attends the 2024 Film Independent Spirit Awards

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James Marsden’s Omega Speedmaster Moonphase

Everybody knows the Moonwatch, but Omega also makes several more complicated versions of its famous Speedmaster chronograph. James Marsden rocked a particularly cool one at the 2024 Film Independent Spirit Awards: The Omega Speedmaster Moonphase is housed in a 42.25mm 18K Sedna Gold case with a black ceramic bezel and a Ceragold tachymeter scale. Its triple-register chronograph display has been altered, however, to accommodate a (hand-engraved!) moonphase display at 6 o’clock; a combined date and running seconds display at 9 o’clock; and a combined hour and 60-minute register at 3 o’clock. Powered by one of Omega’s excellent Co-Axial Master Chronometer movements, it’s a cool, left-of-center take on one of watchmaking’s certified classics.

Jeremy Allen White attends the 30th Annual Screen Actors Guild Awards

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Jeremy Allen White’s Tiffany & Co. Cocktail Watch

In an unusual move (that’s becoming less unusual these days), Jeremy Allen White paired his cream-colored suit to a ladies’ cocktail watch from Tiffany & Co. Not that we have any objections to this resplendent, diamond-covered piece: Crafted from rose gold and bedecked in .85 carats of brilliant-cut diamonds, its white guilloché dial with Roman numeral indices and just two spade-shaped hands is the sort of thing that filled 20th-century watchmaking with so many beloved classics. And as for men wearing teeny women’s watches? It’s a thing now—and we only see it becoming thing–ier.

Josh Hartnett winner of the Outstanding Performance by a Cast in a Motion Picture award for 'Oppenheimer' poses in the...

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Josh Hartnett’s IWC Portofino Automatic

Accepting a SAG Award for Outstanding Performance by a Cast in a Motion Picture for Oppenheimer, Josh Hartnett paired an elegant dinner jacket with an equally classy dress watch from IWC, the Portofino Automatic. Measuring 40mm in stainless steel and featuring a white dial with applied indices, a matching feuille handset, a date window at 3 o’clock, and 30m of water resistance, it’s atypical fare for the International Watch Company, which is more well known for its high-flying, tough-as-nails pilot’s watches. But the Schaffhausen-based marque is a versatile and historic company with wide-ranging product families; the Portofino, available in numerous iterations, is proof that IWC knows how to dress for the party.

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