Teddy Baldassarre
Our Favorite Watches at the 2026 Oscars
Tonight is the grand finale of this year's awards season, with the 98th Academy Awards closing things out with a bang. With almost more glamour, fashion, and celebrity than the average mortal can stand, all these ingredients add up to one of the most exciting watch-spotting nights of the year. We put our editors to the task of combing through wrists on the red carpet for the most compelling, shocking, surprising, and awe-inspiring watches in the game, which they have so graciously curated for your viewing pleasure down below. Let us know your favorite in the comments section! Matt Friend: Rolex Cosmograph Daytona (Ref. 126518LN) Comedian and actor (and watch shopping guest) Matt Friend wears a yellow gold Rolex Daytona Ref. 126518LN which debuted last year in 2025 and is a little special due to its combination of a yellow gold case and a turquoise lacquer dial that evokes the highly collectible vintage “Stella” dials. Hudson Williams: Bulgari Serpenti Tubogas Heated Rivalry star Hudson Williams wears a Bulgari Serpenti Ref. 103434 in steel with a single coil and diamond-set face, retailing for $11,200. Kevin O'Leary: Cartier Crash Skeleton and A Ruby-Set Rolex Daytona Kevin O’Leary double-wrists with a platinum Cartier Crash Skeleton Ref. W7200001 and an off-catalog Rolex Daytona Ref. 126599 TRU done in white gold with baguette-set rubies on the bezel and dial. Leonardo DiCaprio: Rolex 1908 Platinum Rolex Testimonee and Best Actor nominee for his work in One Ba...