Lily Allen hosts star-studded Christmas party at Stringfellows with Olivia Rodrigo in Santa-inspired look

Lily Allen hosted a glitzy Christmas party at London's Stringfellows on Saturday, turning up the heat despite the winter chill in a Santa Claus-inspired ensemble. The 40-year-old singer arrived in a red velvet minidress with white fur trim, a matching long coat, white stockings, and a ruffled garter belt, heightening the festive mood with sky‑high platform heels. Ahead of the event, she treated herself to an exclusive facial from Shane Cooper, a nod to prep that often accompanies high-profile appearances. Once inside, she took to the dance floor with friends before stepping up to the mic to perform for her guests, signaling a night that blended holiday cheer with party‑ready glam. The party drew a host of famous faces, and Allen’s energy set the tone as she moved through a crowd that included fellow pop star Olivia Rodrigo.

Olivia Rodrigo arrived in a striking, leg‑skimming black lace mini dress that hugged every inch of her frame, a look that underscored her status as a rising pop icon and party guest. Rodrigo’s appearance added star wattage to the festive night, which also featured Lola Young in a plunging leather top paired with tiny matching hotpants, while Ella Eyre drew attention in a sheer red gown displaying a lacy under layer. The ensemble diversity mirrored Stringfellows’ reputation as a hotspot where fashion, music, and nightlife collide. Allen kept the spotlight on the dance floor, mingling with friends and guests as the room filled with the kind of energy that has defined the club’s reputation for decades.

The guest list extended beyond Rodrigo and Allen’s circle. Lola Young continued to be a talking point with her daring look, and Lottie Moss attended in a halterneck satin mini dress paired with tights, weaving through the party with a smile. The event also featured a theatrical touch as the London Gay Men’s Chorus arrived to serenade the guests, adding a communal, festive element to the night. As the music swelled and the room hummed with chatter, the singer’s inner circle grew close, with moments captured of carefree lounging on velvet sofas and candid exchanges among friends.

Among the most talked-about moments was Allen’s relaxed display with Jonah Freud, who joined the gathering not long after a dinner date was spotted with the writer, who is the son of Caroline Hutton and PR executive Matthew Freud. The duo were photographed sitting close on a velvet sofa, with Freud’s hand resting on Allen’s thigh as they posed for pictures. The pairing arrived amid ongoing public attention around Allen’s personal life since her split from ex-husband David Harbour in 2020, a chapter that has also been explored in her music.

The Freud connection has added another layer to Allen’s social circle, which has increasingly intersected with notable media and art figures. The party came at a time when Allen has been spending more time with the Freud family, including casual sightings with Charlotte Freud, the granddaughter of Rupert Murdoch’s media empire, on a separate Christmas outing. The star has been navigating personal changes while maintaining a high‑profile musical presence, a balance reflected in her recent release West End Girl, a project described in interviews as exploring the end of her marriage and the complex emotions that followed.

The track Madeline, at the album’s emotional core, has been a focal point of public discussion. Lily described the song as part of a larger artistic exploration, while media outlets have traced it to a potential real-life inspiration. In a Times interview, she said Madeline is a fictional character, though reporting from the Mail on Sunday later claimed a real person was identified behind the name. Natalie Tippett, a costume designer, was named in reports as the person behind the Madeline pseudonym, a claim Tippett publicly denied in a series of Instagram posts. Lily has said she uses artistic license in her storytelling, emphasizing that the album reflects personal experience rather than a literal reenactment of events. The overlap between art and life has kept fans and commentators attentive to the album’s narrative.

The night at Stringfellows also reflected Allen’s ongoing public profile as a performer and a celebrity with close ties to influential circles in music and media. The event’s blend of glamour, music, and festive performance emphasized a year-end moment of visibility for Allen as she continues to chart a path distinct from her previous marriage and public personal history. As she continues to share new music and appearances, the Star’s festive party underscored the enduring public interest in both her career and her evolving personal story, with appearances that suggest a continued prominence in culture and entertainment circles.