Anna Wintour’s Biggest Feuds Over the Years: Billy Porter, Drake and More

Deal of the Day

Anna Wintour has racked up a few foes.

A number of celebrities have made their issues with the Vogue editor-in-chief public, speaking out about her in interviews or dissing her in music.

Wintour has garnered a reputation for being stern with her likeness being portrayed by Meryl Streep in the classic film The Devil Wears Prada. The movie, which is based on former Vogue assistant Lauren Weisberger’s book by the same name, follows Anne Hathaway’s Andrea Sachs as she works for Runway magazine’s editor-in-chief Miranda Priestly — a cold workaholic who doesn’t understand boundaries. (When Wintour learned the book was being turned into a film, she told Vogue’s managing editor Laurie Jones“I cannot remember who [Weisberger] is,” per Amy Odell’s Anna: The Biography.)

While Streep stressed that her character was not directly inspired by Wintour, many say otherwise. Through the years, big names have come forward with alleged examples of Wintour’s not-so-nice behavior.

Keep scrolling to read about Wintour’s biggest feuds:

In August 2023, Porter called Wintour a bitch while discussing his strong feelings about Harry Styles’ Vogue December 2020 cover.

Porter opened up about his disappointment in an interview with The Telegraphaccusing Vogue of not recognizing the LGBTQ+ community’s impact on the fashion industry when the magazine put Styles, a “straight man,” on the cover in a dress. (Styles has previously refused to label his sexuality.)


Porter argued, “It’s not Harry Styles’ fault that he happens to be white and cute and straight and fit into the infrastructure that way … I call out the gatekeepers.”

“It doesn’t feel good to me,” Porter shared. “You’re using my community  — or your people are using my community — to elevate you. You haven’t had to sacrifice anything.”

Porter explained that he was especially hurt considering he participated in an inclusivity Q&A with Wintour six months prior to Styles’ cover debut. “That bitch said to me at the end, ‘How can we do better?’” Porter told The Telegraph.

“And I was so taken off guard that I didn’t say what I should have said.” Porter wishes he would have encouraged Wintour, 73, to “uplift the voices of the leaders of this de-gendering of the fashion movement.”

The rapper trolled Wintour throughout his It’s All a Blur tour with 21 Savage. At the Madison Square Garden show in New York City in July 2023, a graphic of what looks like Wintour with a bloody mouth and gold teeth could be seen plastered on the big screens as Drake rapped on stage. The Wintour look-alike — who rocked a bob with blunt bangs just like the famous journalist — also let out a wicked laugh.

The visuals were displayed as Drake belted out his hit “Jimmy Cooks,” which features the lyric, “Bitch, don’t tell me that you model if you ain’t been in Vogue.”

While it is not immediately clear whether Drake and Wintour are truly at odds, Drake faced a lawsuit from Condé Nast back in November 2022. Drake and 21 Savage were sued by the media company over their use of a fake Vogue magazine cover they created to promote their joint album, Her Loss.

Condé’s general counsel William Bowes spoke out about the matter at the time, per Billboard and Variety, sharing, “As a creative company, we of course understand our brands may from time to time be referenced in other creative works.”


The lawsuit, which was filed in Manhattan federal court, claimed that “Vogue magazine and its editor-in-chief Anna Wintour have had no involvement in Her Loss or its promotion, and have not endorsed it in any way.” The documents continued: “Nor did Condé Nast authorize, much less support, the creation and widespread dissemination of a counterfeit issue of Vogue, or a counterfeit version of perhaps one of the most carefully curated covers in all of the publication business.”


A federal judge eventually ruled in Vogue’s favor, forcing Drake and 21 Savage to get rid of the fake Vogue cover. Drake and 21 Savage settled the lawsuit in February for an undisclosed amount, Variety reported.

While the Kardashian sisters have dominated the Met Gala red carpet in recent years, it is believed that Wintour didn’t always want the family on the guest list. Ahead of Kim’s first ball in 2013, reports surfaced that Wintour didn’t approve of reality stars. Kim made the cut on a technicality, attending the event as then-husband Kanye West’s plus-one. One year later, Kim landed the cover of Vogue with West and North.

When discussing the cover, Wintour seemingly complimented and dissed Kim at the same time.

“I see the role of Vogue to reflect what’s going on in the culture,” she told Fashionsta in 2014. “The first celebrity that I put on the cover of Vogue was Madonna, and that was considered completely controversial at the time, too. It’s such a long time ago probably no one remembers, but she was a very controversial figure. Now she’s part of the establishment. I think if we just remain deeply tasteful and just put deeply tasteful people on the cover, it would be a rather boring magazine. Nobody would talk about us. It’s very important that people do talk about us.”


That same year, Kendall Jenner walked the met carpet with Kris Jenner following suit in 2015. Kylie made her Met debut in 2016 and Khloé and Kourtney attended for the first time in 2022.


Despite some backhanded comments and rumored issues, the Kardashian seem to be on good terms with Wintour. Most recently, Kim graced the cover of Vogue’s March 2022 issue.

Tension between Gunn and Wintour started when Gunn wrote in his 2010 book that Wintour opted to be carried out of a New York fashion show rather than ride an elevator with the public. “We ran over to [an] elevator bay to see if Anna would deign to get on. Then…what did we see but Anna being carried down the stairs…bodyguards had made a fireman’s lock and were racing her from landing to landing.”

After the story came out, “All hell broke loose … Her office was insisting I print a retraction,” he said. Gunn refused to take back what he said, which further strained their relationship. “I don’t look her in the eyes, because I will be turned into stone,” he told Page Six in September 2014.


The following year, Gunn revealed their relationship was still “hostile.”


”She’s a history revisionist, in her mind it never happened basically,” Gunn told Meredith Vieira in September 2015. “May I also add [that] I have huge respect and regard for Ms. Wintour’s charitable work. It’s wonderful and my hat’s off to her but I just wish that she navigated the world with a little more respect for other people.”

Following Talley’s death in January 2022, Wintour released a statement honoring her longtime friend. Wintour acknowledged that the pair had a “complicated” relationship in recent years but took the opportunity to call out Talley’s boundary-breaking impact on the industry.

“All I want to remember today, all I care about, is the brilliant and compassionate man who was a generous and loving friend to me and to my family for many, many years, and who we will all miss so much.”

In 1982, Talley accepted a role as the fashion news director at Vogue. That same year, Wintour was named Vogue’s creative director. The duo climbed the ranks together, with Talley eventually being appointed as the creative director and Wintour as the editor-in-chief. Talley served as the creative director from 1988 to 1995 and went on to be the publication’s editor-at-large from 1998 to 2013, before exiting.

While Wintour and Talley spent many years as close friends, they dealt with their fair share of conflict, namely after Talley was removed from his role hosting the Met Gala red carpet in 2018. While talking about his autobiography, “The Chiffon Trenches: A Memoir,” on CBS This Morning in May 2020, Talley explained that his relationship with Wintour hit “an iceberg.”


In the book, he called Wintour “ruthless” and incapable of “simple human kindness.” He alleged that he was dismissed as Met host for being “old, overweight, uncool.”

Despite their issues, the two are believed to have made amends prior to Talley’s passing.