Leighton Meester and Kelly Rutherford sat front row together at Milan Fashion Week.
The “Gossip Girl” alums, 40 and 57, appeared side by side at Max Mara’s spring 2027 presentation Thursday in Italy’s fashion capital. Both stars channeled their former Upper East Side personas through sharply tailored looks and matching dark shades.
Meester opted for a crisp white button-down paired with a green sequined midi skirt. Rutherford went the monochrome route in a black cashmere car coat worn fully fastened at the neck. Each finished the look with swept-up hair and sunglasses, a styling choice that would have earned Blair Waldorf’s approval.
The public appearance marked a rare scheduling alignment for the two actresses, who portrayed mother and daughter Lily van der Woodsen and Blair Waldorf across six seasons of the CW hit. They were last photographed together at Elie Saab’s spring 2026 show roughly a year prior.
Rutherford has cultivated a significant fashion-world presence since her series ended, amassing a following through regular elevator selfies that highlight her extensive collection of luxury pieces and multiple Birkin bags. Her personal style obsession predates the influencer era by decades.
“I’ve always been very much a minimalist in many ways, but I like beautiful things,” Rutherford said Style in April. “Because of acting, I’ve played dress-up a lot.”
That passion occasionally bled directly into her television work. Rutherford previously revealed that she supplied some of her own designer wardrobe for Lily’s on-screen looks during the original “Gossip Girl” production.
“At the time when we started, there was no RealReal or Vestiaire,” she explained earlier this year. “With certain things, you just couldn’t find them everywhere like you can today. So I just pulled in a few of my things here and there.”
The Max Mara outing comes amid renewed attention to the “Gossip Girl” universe. Blake Lively, who starred as Serena van der Woodsen, recently shared previously unseen behind-the-scenes photographs from the original series set through her social media channels.
The reunion also lands during a season of cast overlap at European fashion weeks. While Meester and Rutherford occupied Milan’s front rows, other former co-stars have surfaced at competing events elsewhere on the continent.
The original “Gossip Girl” ran from 2007 to 2012 and spawned a short-lived HBO Max reboot that premiered in 2021. Meester has since focused primarily on music and selective acting projects, while Rutherford has leaned into her fashion influencer pivot.
Neither actress has publicly commented on their joint appearance at Thursday’s show through personal social media channels as of press time.
Max Mara’s spring 2027 collection presentation drew additional celebrity attendees beyond the former CW stars, though the “Gossip Girl” pairing dominated early coverage from the Italian runway.
The Milan Fashion Week calendar continues through the weekend with additional scheduled presentations.