Kylie Jenner and Timothée Chalamet’s Red Carpet Debut at the 2025 David Di Donatello Awards

While we’ve caught glimpses of Kylie Jenner during awards season—inside ceremonies, courtside at the Lakers with Timothée Chalamet—this red carpet moment at the David Di Donatello Awards in Rome felt like the couple’s soft-launch graduation into something far more official. And while Timmy was honoured for A Complete Unknown, the real treat was seeing the two turn up to Cinecittà Studios looking this coordinated.

There’s something satisfying about the synchronicity. It felt deliberate without being too try-hard. Kylie’s Schiaparelli Fall 2025 gown in fabric printed with the Maison’s signature codes, managing to be both elegant and slightly surreal. I do think one statement earring would’ve served her better than two—it’s Schiaparelli, after all, and their accessories can be overwhelming—but she still looked statuesque.

As for Timmy—this is the version of him I missed. The A Complete Unknown press tour looks were giving whiplash, so it was nice to see him retreat to the comfort of something sharp and timeless. His Tom Ford by Haider Ackermann suit was sleek and refined, anchored by a double-breasted cut and a frozen white gardenia on the lapel. A simple flourish, but one that felt romantic (when in Rome).

Whether you ship them or not, this was a moment.

FTC Disclaimer: Keep in mind that I may receive commissions when you click links and make purchases. However, this does not impact my reviews.