The couple steps out in coordinated looks for a courtside date night, mingling with stars and soaking up the playoff action at Madison Square Garden.
Kylie Jenner and Timothée Chalamet are proving once again that they’re not only Hollywood’s hottest couple—but also among the most stylish.
On Thursday, May 29, the power duo made a courtside appearance at Madison Square Garden for Game 5 of the Eastern Conference Finals between the New York Knicks and the Indiana Pacers. Dressed in coordinated orange-toned outfits, Jenner and Chalamet brought a touch of star power to the pivotal matchup, which the Knicks needed to win to stay in the series.
The 27-year-old Kylie Cosmetics mogul turned heads in a bold leather orange jacket featuring white trim and zipper details, which she paired with a white crop top and sleek black leather pants. Once courtside, she removed the jacket, letting her minimalist yet striking ensemble shine.
Meanwhile, Wonka star Timothée Chalamet, 29, complemented her look with a sporty orange and blue bomber jacket, worn over a black tank top and dark jeans. He finished the look with a silver chain, subtly blending edgy fashion with laid-back Knicks pride.
Their courtside companions for the evening included actor Miles Teller and wife Keleigh Teller, as well as longtime Knicks fan Ben Stiller. Stiller, who previously attended a May 10 playoff game with Chalamet, was spotted celebrating an intense moment during the game, standing in excitement alongside the actor.
Adding to the eventful evening, a now-viral video captured Chalamet and Jenner meeting NBA legends Charles Barkley and Kenny Smith. In the clip, shared by Bleacher Report, Barkley greeted Chalamet warmly: “Continued success, brother,” he said, before thanking the actor for “taking care” of their mutual friend and TNT co-host Ernie Johnson.
Chalamet’s courtside presence has become something of a playoff tradition this season, reflecting his deep-rooted fandom for the Knicks. The actor and Jenner have been spotted at several postseason games, including a recent matchup between the Knicks and the Boston Celtics earlier in May, where they were joined by Jenner’s sister, Kendall.
The couple, who first sparked dating rumors in 2023, have kept much of their romance low-key while making rare but memorable public appearances. Earlier this month, they made their red carpet debut together at the 70th David Di Donatello Awards in Italy. Jenner stunned in an all-black gown, while Chalamet opted for a sleek black tux—both embracing understated elegance.
In an interview with Harper’s Bazaar published the same day as Game 5, Jenner shed light on her preference for wearing black to her boyfriend’s events.
“Although these are the most beautiful, iconic gowns that I’ve been wearing, I think a black dress is also kind of like, not too attention grabbing in the best way,” she said. “You can never go wrong with a black dress.”
With their chemistry, coordinated style, and growing list of high-profile outings, Jenner and Chalamet continue to charm fans both courtside and beyond—bringing star wattage to every scene they enter.
