Jill Demling, Anna Wintour’s former assistant, has revealed the Vogue editor’s daily afternoon coffee milkshake habit and how Beyoncé’s first cover came down to a scheduling fluke.
Demling, now a top casting director, shared the details on Amy Odell’s “Back Row” podcast. She joined Wintour’s office in June 1998 at age 24, when the British-born fashion legend was a decade into her 37-year run as editor-in-chief of American Vogue. Demling would go on to book the magazine’s celebrity covers for nearly two decades.
“At 4 o’clock, she always wanted her coffee milkshake, and we got that at Burger Heaven,” Demling said on the podcast. “It was so good.”
The routine faced disruption in 1999 when Condé Nast moved Vogue’s offices from 350 Madison Avenue to 4 Times Square, leaving no Burger Heaven nearby. Wintour, 77, settled for the closest substitute: a Starbucks Frappuccino, though she had reservations at first.
“She was a bit concerned about not having enough calories,” Demling said of the new drink. The editor apparently adjusted — Starbucks cups appeared throughout most scenes of 2016’s Met Gala documentary “The First Monday in May.”
Wintour’s food and drink preparations still fall to her assistants. More recent staffers told Vogue’s “The Run-Through” podcast in April that they set up her coffee and breakfast before she arrives 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 as a junior assistant and later channeled the experience into her 2003 novel, “The Devil Wears Prada.”
The 2006 film adaptation starred Meryl Streep as Miranda Priestly, the icy fashion editor widely viewed as Wintour’s fictional counterpart. Leslie Fremar, Demling’s junior who moved up to first assistant, confirmed in April that she inspired Emily Blunt’s high-strung Emily character.
Demling said the film captured some truths. “She never yelled, and they got that right,” she said. “But she doesn’t throw coats and bags either.”
With her promotion, Demling took charge of cover star selection during an era when Vogue was swapping models for movie stars. The ideal candidate, she said, was someone like Nicole Kidman — an actress who loved fashion and made what Demling called “Vogue films,” meaning period pieces, musicals and adaptations of famous novels such as “Moulin Rouge” and “The English Patient.”
Romantic comedies and TV stars rarely qualified. Jennifer Aniston landed her first cover for the indie drama “The Good Girl,” not for “Friends.” Pop stars faced the steepest climb. “Music was not her thing,” Demling said of Wintour.
Beyoncé didn’t secure her first Vogue cover until April 2009, and only because scheduled cover star Katherine Heigl dropped out after her film’s release was delayed. Demling recalled that Beyoncé, then 27, had the thriller “Obsessed” coming out and suggested her as replacement.
Her attachment to the film was “the only reason” Wintour approved her, Demling said.
By the September 2015 issue, the dynamic had flipped. Beyoncé had enough leverage to decline an interview and demand photo approval — a control she has maintained ever since.
Is Wintour pleased? “No, she’s not okay with it,” Demling said. “But it’s Beyoncé.”
Demling, who calls herself “talent first,” grasped why stars wanted control. “It’s your image,” she said.
She traced that lesson to Avril Lavigne, who at 16 turned down a Vogue shoot with Steven Meisel because it meant surrendering her hair and makeup to the photographer’s team, Pat McGrath and Garren. The “Complicated” singer preferred her signature black eyeliner and straight hair herself. “She didn’t want to be seen any other way,” Demling said.
Demling continues to work in casting, drawing on nearly two decades inside Wintour’s orbit.
