Anna Wintour used to drink a milkshake every afternoon, according to her former assistant

See more of our coverage in your search results. Anna Wintour arrives for the Met Gala on May 2, 2022, in New York. A former assistant recalled Wintour drank a daily coffee milkshake in the ’90s. Gilbert Carrasquillo The devil drinks… milkshakes? Anna Wintour once powered through her afternoons with a daily coffee milkshake, according to her former assistant Jill Demling. “At 4 o’clock, she always wanted her coffee milkshake, and we got that at Burger Heaven,” Demling said on Amy Odell’s “Back Row” podcast. “It was so good.” “It was so good,” former Vogue staffer Jill Demling said of the Burger Heaven treat on Amy Odell’s “Back Row” podcast. Getty Images for 2026 Teen Vogue Fest After Condé Nast relocated to Times Square, the editor switched to Starbucks Frappuccinos. WireImage Demling, now a top casting director, joined Wintour’s office in June 1998, when the British-born fashion legend was a decade into her 37-year run as editor-in-chief of American Vogue. Demling was 24 at the time and went on to book the magazine’s celebrity covers for nearly two decades. The afternoon routine hit a snag in 1999 when Vogue’s publisher Condé Nast moved its offices from 350 Madison Avenue to 4 Times Square, where there was no Burger Heaven nearby. So Wintour, 77, made do with the nearest substitute: a Starbucks Frappuccino — though she wasn’t entirely sold on it initially. “She was a bit concerned about not having enough calories,” Demling said of the new drink. She seemingly came around: Starbucks cups turned up in most scenes of 2016’s Met Gala documentary “The First Monday in May.” Hired at 24, Demling later spent nearly two decades booking Vogue’s celebrity cover stars. WireImage Demling helped hire Lauren Weisberger, who turned her time in the office into “The Devil Wears Prada.” Instagram/jilldemling Wintour’s food and drink still fall to her assistants. The editor’s more recent staffers told Vogue’s “The Run-Through” podcast in April that they set up her coffee and breakfast before she arrives at the office around 8 a.m. When Demling was promoted at the end of 1999, she helped hire her replacement. One candidate was Lauren Weisberger, who joined Wintour’s office as a junior assistant — and later turned the experience into her 2003 novel, “The Devil Wears Prada.” The 2006 hit film adaptation starred Meryl Streep as Miranda Priestly, the icy fashion editor widely seen as a stand-in for Wintour. Leslie Fremar, Demling’s junior who moved up to first assistant, confirmed in April that she was the inspiration for Emily Blunt’s high-strung Emily. Demling said the film had some moments of truth. “She never yelled, and they got that right,” she said. “But she doesn’t throw coats and bags either.” “She never yelled, and they got that right,” Demling said of Meryl Streep’s onscreen editor. REUTERS Wintour preferred movie stars from fashion-forward films, and rarely gave covers to rom-com and TV actresses. Musicians were even rarer. Corbis via Getty Images Demling, meanwhile, had a new assignment: deciding who landed on Vogue’s covers at a time when the magazine was trading models for movie stars. The ideal cover star in those years, Demling said, was someone like Nicole Kidman, an actress who loved fashion and made what she called “Vogue films.” That meant the kind of movies Wintour liked: period pieces, musicals and adaptations of famous novels, such as “Moulin Rouge” and “The English Patient.” Romantic comedies and TV stars rarely made the cut. Demling said that’s why Jennifer Aniston got her first cover for the indie drama “The Good Girl” and not for “Friends.” Pop stars had an even harder time. “Music was not her thing,” Demling said of Wintour. Beyoncé didn’t land her first Vogue cover until April 2009, and only because Katherine Heigl, the scheduled cover star, backed out after her film’s release was pushed. Demling remembered that Beyoncé had a movie coming out, the 2009 thriller “Obsessed,” and suggested the then-27-year-old star as a replacement. Her attachment to the film was “the only reason” Wintour gave her the green light, Demling said. Beyoncé got her first Vogue cover in 2009 as she was promoting her film “Obsessed.” She landed the spot after Katherine Heigl dropped out. Vogue For her September 2015 cover, the singer had enough leverage to decline an interview and win final sign-off on her images Vogue By the time the singer covered the September 2015 issue, the balance of power had shifted, and Beyoncé had enough leverage to decline an interview and demand approval over her photos. Demling said that by then, Vogue “needed her probably more” than she needed the magazine. Beyoncé has kept final sign-off on her images ever since. Is Wintour thrilled about the arrangement? “No, she’s not okay with it,” Demling said. “But it’s Beyoncé.” Demling, who calls herself “talent first,” understood why stars wanted a say. “It’s your image,” she said. She said she learned that from Avril Lavigne, who turned down a Vogue shoot with Steven Meisel at 16 because it meant giving up her own hair and makeup to the photographer’s go-to team, Pat McGrath and Garren. The “Complicated” singer preferred to do her signature black eyeliner and straight hair herself. “She didn’t want to be seen any other way,” Demling said. Community Guidelines Welcome to the Page Six Community! Our community is about connecting people through open and thoughtful conversations. We want our readers to share their views and exchange ideas in a safe space. In order to do so, we've created a simple set of rules that will improve your experience. Simply put, keep it civil. 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