Anna Wintour's Former Assistant Spills Her Daily Coffee Milkshake Habit

Anna Wintour drinking a coffee milkshake every afternoon at 4 p.m. is the mental image we didn’t know we needed. Her former assistant Jill Demling shared the detail on Amy Odell’s“Back Row”podcast, explaining that the Vogue editor ordered that exact treat from Burger Heaven daily. When Condé Nast relocated to Times Square in 1999, the milkshake was replaced by Starbucks Frappuccinos, and Wintour apparently had some concerns about the calorie count.

The podcast had more than dessert talk. Demling started in Wintour’s office in 1998, later booked celebrity covers for nearly two decades, and even helped hire Lauren Weisberger, whose time at Vogue inspired“The Devil Wears Prada.”She also recalled that Beyoncé’s first Vogue cover in 2009 only came together because Katherine Heigl backed out at the last minute.

By 2015, Beyoncé had flipped the script entirely, declining an interview and demanding photo approval for her cover. The story tracks a full power shift in magazines, from editors calling the shots to celebrities writing their own rules. So what’s your daily 4 p.m. ritual that you’d never give up? Tell us in the comments.