Leighton Meester and Kelly Rutherford were recently spotted together at Milan Fashion Week. The former Gossip Girl co-stars sat side-by-side during the Max Mara spring 2027 runway show on Thursday.

Max Mara's front row features Blair and Lily in Milan

The Max Mara spring 2027 runway show in Milan provided an unexpected moment of nostalgia for fans of the hit series Gossip Girl. As reported by the source, Leighton Meester and Kelly Rutherford occupied adjacent seats in the front row, bringing a touch of Upper East Side elegance to the Italian fashion capital.

The actresses' styling appeared to pay homage to their most famous roles. Meester wore a column-silhouette ensemble consisting of a white tie-up blouse tucked into a sequined skirt featuring a green-to-black gradient. Her look, described as having an "office-ready finish," felt like a direct nod to the character of Blair Waldorf, who ended the series as a high-powered fashion executive at Waldorf Designs.

Rutherford, playing the sophisticated Lily van der Woodsen, opted for a more minimalist approach. She wore a knee-length jacket and a trenchcoat in a stark all-black palette, accessorized with geometric sunglasses. To add a pop of color, she carried a burgundy Max Mara purse, a nod to the character's penchant for luxury statement bags like Birkins and Kellys.

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A sartorial nod to the 2007-2012 Gossip Girl era

This reunion serves as a stylish reminder of the cultural impact of Gossip Girl,which ran from 2007 to 2012. The show's aesthetic—a blend of prep-school chic and high-society luxury—continues to influence modern fashion trends and remains a touchstone for internet culture.

The connection between the actresses' real-life presence and their characters' trajectories is striking. While the show's narrative saw Blair Waldorf ascend the fashion ladder and Lily van der Woodsen maintain her status as a luxury socialite, the two women have transitioned into the real-world fashion circuit as respected figures. Their appearance at a Max Mara show reinforces the lasting link between the show's leacy and the contemporary fashion industry.

From Falconeri in LA to Elie Saab in Paris

While this Milan encounter was a highlight, it is part of a larger pattern of Gossip Girl cast members reconvening at global fasshion events. Earlier this year, Meester was seen at a dinner for the Italian label Falconeri in Los Angeles with her former co-star Chace Crawford, who played Nate Archibald. Additionally, the report notes that Meester and Rutherford were photographed together at Elie Saab’s runway show in Paris in March 2025.

However, several questions remain regarding the nature of these gatherings. It is unclear if these reunions are spontaneous coincidences occurring within the same elite social circles or if they represent a more coordinated effort by the cast to engage with their fanbase.. Furthermore, while the stars maintain an amicable relationship, fans are left wondering if more cast members will join these high-profile fashion week appearances in the future.