Charli XCX dresses up as sexy secretary Lee Holloway from the erotic Noughties film for Kendall Jenner's star-studded Halloween bash (but the host keeps her look under wraps!)

The annual Halloween celebration hosted by Kendall Jenner at Bar Marmont in Los Angeles once again attracted a constellation of celebrities, with Charli XCX making a striking entrance that set her apart from the typical seasonal fare. Steering clear of conventional costumes like witches or Playboy bunnies, the British singer embraced a bold cinematic reference by dressing as Lee Holloway, the protagonist from the 2002 erotic thriller "Secretary," originally portrayed by Maggie Gyllenhaal.

Charli's costume was a faithful homage to the character’s signature look, featuring a sheer white blouse paired with a sleek black pencil skirt. The ensemble was further accentuated by a notable arm bar, an accessory integral to the film’s narrative and symbolic of the complex dynamics between Holloway and her dominant employer, played by James Spader. This choice of attire sparked enthusiasm among fans, who praised Charli for her distinctive and thoughtful nod to cult cinema.

While many attendees enthusiastically showcased their Halloween costumes, Kendall Jenner herself remained discreet about her outfit, opting for a low-profile departure from the event. Attendance included a diverse group of celebrities such as model Vittoria Ceretti, social media influencer Alix Earle, and musician Finneas, brother to Billie Eilish, each bringing their own creative flair to the festivities.

Beyond the party circuit, Charli XCX is extending her influence into the fashion world through a charitable initiative involving a curated sale of her tour wardrobe on Vinted. This endeavor is designed to benefit Rainbow Railroad, an organization dedicated to assisting LGBTQ+ individuals facing persecution worldwide. The collection features a range of pieces—from stage-worn outfits to carefully selected vintage items—that reflect Charli's eclectic style and commitment to sustainable fashion.

Her collaboration with longtime stylist Chris Horan involves combing through second-hand fashion markets to discover unique garments, encouraging fans to tag listings with #charlixcx for potential inclusion in future projects. The upcoming sale, scheduled for November 16 across the UK, US, and Australia, promises to offer fans and fashion enthusiasts the chance to own items with rich histories, including a leather jacket by R&M Leathers and vintage T-shirts, alongside notable designer pieces such as a Roberto Cavalli dress worn to high-profile events.

This initiative aligns with Charli’s broader artistic practice of repurposing and reimagining clothing, as demonstrated by her past work involving a reworked wedding dress for a music video and revisiting a Valentino gown previously worn in her "Good Ones" video. By giving garments new life, she champions a sustainable approach to fashion, while creating a narrative that connects her music, style, and social causes.

Returning to the Halloween event, other attendees showcased a variety of imaginative costumes: Vittoria Ceretti appeared as Little Red Riding Hood; singer Tate McRae adopted a Catwoman-inspired leather ensemble; and actress Zoey Deutch embodied the iconic Jessica Rabbit. The event also featured standout looks such as Cara Delevingne’s transformation into Frank-N-Furter from "The Rocky Horror Picture Show," and Justine Skye’s playful interpretation of a Teletubbies character.

The party exemplified the intersection of music, fashion, and celebrity culture, highlighting how costume choices at high-profile events can serve as creative statements. Charli XCX’s decision to draw from a niche film reference not only distinguished her presence but also reinforced her reputation for blending pop culture with avant-garde artistry.

Details surrounding Kendall Jenner’s costume remain scarce, as the host opted for privacy over publicity in her Halloween presentation. Nonetheless, the event’s overall atmosphere and guest appearances underscore its significance as a major social gathering in the entertainment calendar each year.

In summary, Charli XCX’s appearance at Kendall Jenner’s Halloween party was notable for its thoughtful homage to a cult film character, reflecting her multifaceted engagement with music, fashion, and cultural commentary. Concurrently, her charitable wardrobe sale initiative demonstrates an ongoing commitment to social issues and sustainable practices within the fashion industry.