Leighton Meester and Kelly Rutherford Bring a Little Upper East Side to Milan
By Alexus Mosley
Photo Credit: Getty Images
Spotted: two familiar Upper East Siders sitting front row in Milan.
Leighton Meester and Kelly Rutherford reunited at Max Mara’s Spring/Summer 2027 show during Milan Fashion Week, giving Gossip Girl fans the kind of fashion-world crossover we will happily accept at any time. And while the nostalgia was reason enough to pay attention, their outfits made the moment even better.
Meester arrived in a crisp white long-sleeve shirt tucked into a shimmering black-and-gold sequined midi skirt. The combination was classic on top and party on the bottom, with a wide black waistband creating a sharp, almost corseted effect through the middle. She finished the look with black peep-toe pumps, oversized black sunglasses, and a roomy dark leather tote. Her hair was swept into a relaxed updo with wispy bangs, while a glossy red manicure added one tiny pop of color.
Basically, businesswoman who has dinner reservations immediately after the meeting. So Blair!
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Rutherford took the opposite approach, going beautifully monochromatic in an oversized black double-breasted coat with a high neckline and sculptural, cape-like proportions.
She paired the coat with pale pointed-toe heels, angular black sunglasses and a burgundy handbag, giving the otherwise minimal look just enough contrast. With her hair pulled neatly back, the whole thing felt sleek, expensive, and very Lily van der Woodsen casually leaving a board meeting before lunch at Bergdorf’s.
Together, the looks were a study in contrast. Meester brought sparkle, polish and a little playful glamour, while Rutherford leaned into restrained, grown-up minimalism. Yet somehow, despite dressing completely differently, they looked perfectly coordinated sitting side by side.
Photo Credit: Getty Images
Of course, seeing the women behind Blair Waldorf and Lily van der Woodsen together at a major fashion show was always going to send Gossip Girl fans into a minor spiral. Fashion was practically a supporting character on the series, after all.
But this wasn’t just a nostalgia moment. More than a decade after their Upper East Side alter egos became style references in their own right, Meester and Rutherford are still giving us plenty to talk about from the front row.