A former personal assistant, Lauren Weisberger, wrote the bestselling 2003 roman à clef The Devil Wears Prada, later made into a successful 2006 film starring Meryl Streep as Miranda Priestly, a fashion editor, believed to be based on Wintour.

[33] A few months later, Bradshaw helped her get her first position as a fashion editor, at Viva, a women's adult magazine started by Kathy Keeton, then the wife of Penthouse publisher Bob Guccione.

Mirabella had preferred tight head shots of well-known models in studios; Wintour's covers showed more of the body and were taken outside, like those Diana Vreeland had done years earlier.

[37] She used less well-known models, and mixed inexpensive clothes with high fashion: the first issue she was in charge of, November 1988, featured a Peter Lindbergh photograph of 19-year-old Michaela Bercu in a $50 pair of faded jeans and a bejeweled T-shirt by Christian Lacroix worth $10,000.

Kate Betts, seen as Wintour's likely successor, had broadened the magazine's reach by commissioning stories with a more hard-news edge, about women in politics, street culture, and the financial difficulties of some major designers.

[71] The next month, a lavish Karl Lagerfeld gown she wore to the Met's Costume Institute Gala was called "the worst fashion faux pas of 2008".

At the end of the year, December's cover highlighted a disparaging comment Jennifer Aniston made about Angelina Jolie, to the former's displeasure; media observers began speculating that Wintour had lost her touch.

[85] On the occasion of the 10th anniversary of The Devil Wears Prada's release, in 2016, The Ringer noted how Wintour's personal image had evolved since that film's depiction of Miranda Priestley.

The grievances reflected in the novel and film "[seem] like an increasingly petty complaint when held up against a readership that remains well into the seven figures and the undisputed edge in ad sales that comes with it.

[89] Following the murder of George Floyd, Wintour was reported to have issued an apology to staff for Vogue's complicity in racism, stating the magazine had "not found enough ways to elevate and give space to Black editors, writers, photographers, designers and other creators".

[91] In 2023, Wintour suggested the creation of an event similar to the Met Gala in London to raise funds for the local arts scene, which has struggled to recover in the aftermath of COVID.

[98] In addition, she receives several perks, such as a chauffeured Mercedes-Benz S-Class (both in New York and abroad), a $200,000 shopping allowance,[75] and the Coco Chanel Suite at the Hotel Ritz Paris while attending European fashion shows.

[44] Condé Nast president Samuel Irving Newhouse Jr. had the company make her an interest-free $1.6 million loan to purchase her townhouse in Greenwich Village.

[121] Lauren Weisberger, a former Wintour assistant[122] who left Vogue for Departures along with Richard Story, wrote The Devil Wears Prada after a writing workshop he suggested she take.

"[125] While it has been suggested that the fashion magazine setting and Miranda Priestly character were based on Vogue and Wintour, Weisberger claims she drew not only from her own experiences but those of her friends as well.

[134] During the production of The Devil Wears Prada in 2005, Wintour was reportedly threatening prominent fashion personalities, particularly designers, that Vogue would not cover them if they made cameo appearances in the film as themselves.

In the film, actress Meryl Streep plays Priestly different enough from the book to receive critical praise as an entirely original (and more sympathetic) character.

Edna Mode's similar hairstyle in The Incredibles (2004) has been noted,[77][146] Johnny Depp said he partially based the demeanour of Willy Wonka in Charlie and the Chocolate Factory (2005) on Wintour.

[148] In 2005, two years after The Devil Wears Prada, Oppenheimer's Front Row: The Cool Life and Hot Times of Vogue's Editor in Chief was published.

"[109] Junior staff at Vogue are said to understand, through unwritten rules, that they should not initiate interactions with her; it has been said that they are discouraged from riding an elevator with her, and if they do, should not speak to her, though Wintour has called this an exaggeration.

[37] In a deleted scene from The September Issue, she complains about the "horrible white plastic buckets" of ice behind the bars at the CFDA's 7th on Sale AIDS benefit and moves them out of sight.

"[156] Peter Braunstein, a former Women's Wear Daily media reporter convicted of sexually assaulting a coworker, allegedly planned to kill Wintour because of perceived slights.

[107] She and Vogue publisher Ron Galotti once retaliated for a protest outside the Condé Nast offices during the company's annual Christmas party by sending down a plate of roast beef.

[39] At the 2005 Anglomania celebration, a Vogue-sponsored salute to British fashion at the Met, Wintour is said to have personally chosen the clothes for prominent attendees such as Jennifer Lopez, Kate Moss, Donald Trump, and Diane von Fürstenberg.

[63] She has been credited with killing grunge fashion in the early 1990s, when it was not selling well, by telling designers if they continued to avoid glamour their looks would not be photographed for Vogue.

Amanda Fortini at Slate said she was comfortable with Wintour's elitism since that was intrinsic to fashion: Most of us read Vogue not with the intention of buying the wildly expensive clothes, but because doing so educates our eye and hones our taste, similar to the way eating gourmet food refines the palate.

[39]Emma Brockes sees this in Wintour herself: "[Her] unwavering ability to look as if she lives within the pages of her magazine has a sort of honesty to it, proof that, whatever one thinks about it, the lifestyle peddled by Vogue is at least physically possible.

"Powerful women in the media always get inspected more thoroughly than their male counterparts", said The New York Times in a piece about Wintour shortly after The Devil Wears Prada's release.

Reviewing Oppenheimer's book in the Washington Monthly, managing editor Christina Larson notes that Vogue, unlike many other women's magazines,...doesn't play to its readership's sense of inadequacy ...

Instead, it reminds women to take satisfaction, parading all manner of fineries (clothes, furniture, travel destinations) that a successful woman might buy, or at least admire.