John Mayer Just Wore a Strong Contender for Watch of the Year

There is maybe no watch collector more influential than John Mayer. His Talking Watches got a whole generation hooked on timepieces and everyone he meets ends up with the bug. “I think it’s the same story for most male singer-songwriters,” Ed Sheeran told GQ when asked how he got his start in collecting. “They basically get to know John Mayer.” So it’s always important to keep up with what’s on the musician’s wrist, especially when it’s as unexpected—at least to casual observers—as it was this week.Because despite oodles of rare vintage Rolexes, piles of world-class AP.s, and a rotation without a single dud in it, Mayer chose a modern tool watch to wear while being named The Hollywood Reporter’s Philanthropist of the Year. The piece is strongly in contention for Watch of the Year: Vacheron Constantin Overseas Dual Time. Released during Watches and Wonders in Geneva this past April, it’s part of a collection of four pieces, each of which features a different dial color representing a compass’s cardinal direction: brown for south, white for both, blue for east, and—on Mayer’s watch—green for west.Courtesy of Vacheron Constantin; Getty ImagesThe Cardinal Points sub-collection started as a 2021 limited edition called the Overseas Dual Time “Everest.” That watch was modeled after a special titanium and tantalum watch made for photographer Cory Richards, who brought the watch with him while summiting Everest in 2019. After taking that watch up to the roof of the world, Richards returned it to Vacheron, which auctioned it at Phillips’ Game Changers charity auction. Though it carried an estimate of $20,000 to $40,000, the watch hammered for $106,250, with the proceeds benefitting the National Geographic Society, a longtime partner of Richards.With its history not only of exploration, but also its association with philanthropic causes, the Overseas Dual Time felt like a particularly appropriate choice for Mayer’s wrist as he received the Philanthropist of the Year Award. Heart and Armor, which he co-founded and whose board he chairs, is dedicated to veterans’ issues such as PTSD, sleep health, and civilian-veteran engagement, and has generated a portfolio of more than $13M in scientific research. What better accessory to accompany him than one that already benefitted one of the world’s leading scientific organizations?Shohei Ohtani’s Seiko StartimeNot many individuals can claim to have a special pièce unique made for them—but if you’re Shohei Ohtani, you get a special modelle unique. That’s right—there’s but one Seiko Startime, and it was designed exclusively for #17 of the Los Angeles Dodgers. Called the Startime, its unique movement architecture tracks the passage of one million hours (cue Dr. Evil), signifying the immense amount of time that Ohtani has put into working on his game. Emanating from the dial’s center, successive rotating rings track the passage of 1,000 hours; 10,000 hours; 100,000 hours; and 1,000,000 hours, with elapsed time becoming ever more imperceptible as the resolution decreases. Rendered in titanium and finished with a sapphire crown, it ranks among the most special unique timekeepers ever developed.Drew Brees’ Panerai Radiomir California 3 DaysAppearing on Jimmy Fallon this week, imminent Hall of Famer and former Saints quarterback Drew Brees wore a vintage-inspired favorite, Panerai’s Radiomir California 3 Days. Based upon pieces developed by Panerai for the Italian navy, this positively massive 47mm stainless steel, cushioned-shaped watch features wire-style lugs, an onion-style crown, and the hand-wound Panerai cal. P.3000 movement. The dial—with its black background, outer railroad minute track, and “California”-style mix of Arabic and Roman numerals—recalls the brand’s early partnership with Rolex, which made components for its military watches. (Rolex called this type of dial, which it debuted in the 1940s, “Error-Proof.”)Kevin Hart’s Patek Philippe Nautilus ref. 5810/1G-001Not to be outdone by Brees, Kevin Hart also showed up to Jimmy Fallon’s set ready to play. On his wrist? The new Patek Philippe Nautilus ref. 5810/1G-001. Released at Watches and Wonders 2026, this 50th-anniversary reference is a limited edition of just 2,000 pieces, making it one of the most coveted launches of the year. Measuring 41mm in white gold, it’s just 6.9mm tall by virtue of the ultra-thin, self-winding cal. 240, a longtime mainstay of modern Patek Philippe production. (The gold rotor, visible from the caseback, features a cool engraving: “50 1976-2026.”) Featuring a sunburst blue dial with the Nautilus collection’s classic horizontally embossed pattern, it has no second hand, lending it an incredibly clean look.Tom Brady’s Audemars Piguet RD#5The technical name for Tom Brady’s watch—seen on his wrist at Fanatics Fest NYC 2026 this week— is the Audemars Piguet Royal Oak Extra-Thin Self-Winding Flying Tourbillon Chronograph RD#5…but we’re short on time here so we’re gonna call it the “RD#5,” for short. An A-1 collector, Brady has all sorts of outrageous pieces in his watchbox. That being said, few pieces can best this insane AP: a 150th-anniversary timepiece from 2025, it combines a titanium and BMG case with a flyback chronograph, a flying tourbillon, and a new pusher system that makes it feel like you’re operating a smartphone rather than a mechanical watch.