Over 37 years at American Vogue, Anna Wintour became the world’s most famous editor — a pop-culture icon, even, looming over fashion and media.
Big shoes to fill? Try Manolo Blahnik heeled boots.
Chloe Malle, 40, took over the U.S. magazine in September, and ahead of the release of her first print issue, joined Ms. Wintour, 76, for their first side-by-side interview, published Tuesday by The New York Times.
The conversation focused on their working relationship and Ms. Malle’s efforts to establish her identity while her predecessor remains, quite unusually, her boss. But there were moments of levity, too. Here are five more surprising exchanges.
Sitting with the ‘Devil.’
The seating chart for the Met Gala, the annual fashion fest co-chaired by Ms. Wintour and covered extensively by Vogue, requires diplomatic tact and military precision.
But if they could choose more freely, which A-list guests would Ms. Wintour and Ms. Malle pick as their seatmates?
A tennis superfan, Ms. Wintour wants to be sandwiched between the sport’s top male players, Carlos Alcaraz and Jannik Sinner.
Ms. Malle named Meryl Streep first — a “cheeky” answer, she admitted, given Ms. Streep’s imperial Anna-inspired character in “The Devil Wears Prada” — and Cole Escola, the star and creator of Broadway’s “Oh Mary!”
Another side of Anna?
Ms. Wintour’s stern reputation precedes her. What is she like away from the public eye, though?
Ms. Malle volunteered a warmer portrait, praising Ms. Wintour as “a parent and a grandparent and a friend” who sends condolences to grieving staffers and throws parties at her home for departing colleagues. “You never feel like Anna is too busy,” she said, “to plan something for someone she cares about, or wants to make sure that they feel special.”
The two women have grown close over the last 15 years, even after Ms. Malle tried to quit Vogue in 2016 to focus on her writing. (Ms. Wintour persuaded her to go part-time instead.)
Indeed, Ms. Wintour delivered a pointedly un-devilish message of benevolence and collegiality in the interview: “It’s really important in the world that we work in to be generous and to be kind and to be supportive.”
They recently debated … Miss Piggy.
Miss Piggy was first photographed by Irving Penn for Vogue in 1978, before Ms. Wintour’s time at the magazine.
Nearly 50 years later, she and Ms. Malle debated whether the muppet was right for a recent episode of Vogue’s “Life in Looks,” a series that has previously featured Michelle Obama, Sarah Jessica Parker, Elton John and various Kardashian-Jenners.
Ms. Malle found herself “pleading with Anna,” she said. Pressed for her thoughts, Ms. Wintour demurred: “Um, it’s Chloe’s decision to make.”
Never far from cafeteria cliques.
Ms. Malle was candid about the “high school” mentality of the fashion world. “It’s a very hard industry to feel like you’re the cool person in it,” she said.
Ms. Wintour interjected here, suggesting this perspective was a strength; it makes Ms. Malle seems more real to Vogue’s audience.
Still, “fashion people” wondered why Ms. Malle was missing from Vogue’s Paris delegation at the couture runway shows in January. It seemed like an opportunity for her to grow her profile with advertisers, the press, designers and their elite clients.
“Chloe has a lot going on,” explained Ms. Wintour, who went to Paris in January but said she does not consider it “essential” for every editor to attend every event. “We felt that it was a more important time for her to be here at Vogue, rather than at the shows.”
But as the world increasingly revolves around celebrities and creators with big, marketable personalities, does Condé Nast see value in its new guard becoming stars, too?
“I want editors to be more forward-facing,” Ms. Malle said, citing video and other digital opportunities for subscribers to “connect with us as people.” She already co-hosts Vogue’s podcast, “The Run-Through,” and will soon publish a weekly newsletter called “Malle Wear.”
“Chloe will find her own path about how public or not public she wants to be,” Ms. Wintour said. “But it isn’t for one second that she’s not comfortable in that arena. She entirely is.”
The bob goes on tour.
Freed from her daily responsibilities at American Vogue, Ms. Wintour is “focusing much more on the bigger picture,” she said. She plans to spend more time with international editors, including those in Asia, where she’ll travel “a great deal” in late 2026.
Ms. Wintour said she pushes young leaders to experiment and take risks, even if their bets don’t always pay off, all in service of becoming “voices for their generation.”
This work reminds her a bit of another job that involves scouting and fostering talent. “If I had an alternative career path, and I couldn’t run the Tennis Channel, I would really love to be a theater producer,” she said.
Jessica Testa covers nontraditional and emerging media for The Times.
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