On Monday night, the New York Knicks made playoff and franchise history, clenching an 11-game winning streak in their second shutout series of the playoffs, all while securing a spot in the NBA finals for the first time in 27 years.
It was a triumphant feat that will no doubt be referenced by New York sports fans for the rest of time — kind of like how fashion enthusiasts will never forget the Chanel tote bag Kylie Jenner was boasting courtside. Hey, we all have our Roman Empires, right?
Kylie Jenner and actor Timothée Chalamet attend game four of the NBA Eastern Conference Finals between the Cleveland Cavaliers and the New York Knicks.
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Jenner has been on a winning run of her own these past few weeks, inspiring the next generation of wives and girlfriends of basketball fanatics in a game-ready wardrobe imbued with “cool girl” energy. Next to her partner, Knicks devotee, Timothée Chalamet, the Kylie Cosmetics founder has returned to Madison Square Garden week after week, bringing with her, a collection of kitten heels, low-rise denim, white tank tops and at least one rare find.
Timothée Chalamet and Kylie Jenner on Monday night in Cleveland.
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Monday night’s Eastern Conference Finals in Cleveland called for a croc leather tote bag straight from Matthieu Blazy’s Chanel — a collection that spawned a shopping frenzy upon its release in stores. The bag was paired with lightwash denim and a vintage Knicks shirt, similar to the one Chalamet sported next to her. What some might consider a casual clothing recipe, the outfit was further embellished with diamond earrings and her rock of a pinky ring.
Kylie Jenner react during the third quarter in game two of the second round of the NBA Eastern Conference Playoffs.
At game two of the Knicks versus Philadelphia 76ers series, Jenner showed team spirit in an orange leather motorcycle jacket, The Perfect Tank by Danielle Guizio, Maria Slim Bootcut Tribeca Jeans by EB Denim, vintage Miu Miu lace up kitten heels sourced by Source of Sweet and a glossy Blue Abyss Porosus Crocodile Hermès Birkin. While it may not have been stamped with the official Knicks branding, the outfit was more “rah rah” than she’d previously sported.
Kylie Jenner, and Ben Stiller at the Eastern Conference First Round NBA Playoffs between the Atlanta Hawks and the New York Knicks at Madison Square Garden on April 28.
At game five of the Eastern Conference first round series, Jenner donned a pair of white studded jeans from Isabel Marant’s spring 2013 runway that looked eerily similar to the denim in the Khy “Born in LA” rebrand. The style choice set the internet aflame, with many questioning why she wouldn’t wear the pants from her own label.
Kylie Jenner walks courtside during the third quarter in game five between the Indiana Pacers and the New York Knicks in the 2025 NBA Playoffs.
Despite the online noise, the ensemble was consistent with Jenner’s courtside formula. In 2025, however, most of her remarkable vintage came from the vault of Jean Paul Gaultier or Tom Ford during his Gucci era. There was, of course, the occasional Knicks memorabilia, sourced from the fan archive.
Now, with one more series to go in the 2026 season, fashion fans are gearing up for the final few bites of Chalamet and Jenner’s game-day dress. Will they twin continue to coordinate? Only time will tell. Until then, see here for a closer look at their style as a couple.
