So, has finally decided to hang up her designer heels as Vogue’s editor-in-chief after nearly four decades. As the fashion world collectively clutches its pearls, let’s take a stroll through her most memorable, headline-grabbing, and eyebrow-raising moments.
Spoiler: there’s more to Anna than just sunglasses and that bob.
Wintour’s first American Vogue cover in 1988 was the fashion equivalent of a mic drop. Instead of the usual glammed-up close-up, she put on the cover in faded Guess jeans and a $10,000 Christian Lacroix jacket.
The printers thought it was a mistake. It wasn’t.
Anna could just “sense the winds of change” — and so she delivered a gust. Turns out, you can wear jeans on the cover of Vogue if Anna Wintour approves.
Before Anna, the Met Gala was a nice little fundraiser. Under her rule, it became the most exclusive, over-the-top, meme-generating night in fashion.
She started co-chairing in 1995, moved the event to the first Monday in May, and made the guest list so tight that even A-listers sweat over their invites.
If you weren’t on Anna’s list, you simply didn’t exist (at least not in the world of high fashion).
’s The Devil Wears Prada (book and film) turned Anna into a pop culture phenomenon. Miranda Priestly, with her icy stare and impossible standards, was inspired by Wintour’s own reputation as the ultimate boss-from-hell.
Anna is clearly in on the joke because when attending The Devil Wears Prada musical last year, she did in fact turn up wearing Prada. I see you Anna!
She later told the BBC it’s up to “the audience and the people I work with” to decide if she and Miranda are twinsies.
Remember when and landed the April 2014 cover? The internet basically combusted. Critics called it the end of Vogue’s credibility, Anna called it a business move.
The hashtag #worldsmosttalkedaboutcouple on the Instagram Post said it all.
Kim went from reality TV to fashion royalty overnight, and Anna proved she could still set the agenda — even if it meant ruffling a few (million) feathers.
Anna Wintour was infamous for her meticulous control — down to telling to lose weight for her cover and personally picking outfits for Met Gala guests.
“It was a very gentle suggestion,” Anna said in a 2009 60 Minutes interview.
“I went to Chicago to visit Oprah, and I suggested that it might be an idea that she lose a little bit of weight before she appeared in the magazine.”
Former Vogue editor-at-large also revealed on the Oprah Winfrey Show in 2005 that Wintour had demanded he lose weight as well.
“Most of the Vogue girls are so thin, tremendously thin, because Miss Anna don’t like fat people,” he said.
Anna’s reign wasn’t all sequins and sunshine. She’s faced serious criticism for Vogue’s lack of diversity and for fostering a “thin, rich, and white” standard of beauty. The New York Times reported allegations of a toxic work environment and out of touch editorial decisions, including brushing off concerns about cultural appropriation and using offensive language in internal emails.
Wintour has since apologised, admitting, “Undoubtedly, I have made mistakes along the way, and if any mistakes were made at Vogue under my watch, they are mine to own and remedy and I am committed to doing the work,” per PEOPLE.
In 2017, she was officially knighted — well, damed — by Queen , receiving the title of Dame Commander of the Order of the British Empire (DBE) for her services to fashion and journalism.
She collected her medal at Buckingham Palace, naturally dressed in a pink Chanel coat and, yes, those ever-present sunglasses. Because even the Queen doesn’t get to see Anna’s eyes before noon.
If you’ve ever wondered how Anna Wintour manages to look exactly the same in every photo taken since 1988, the answer is: routine, and lots of it. Her mornings start from 4am to 5am, not with a leisurely scroll through Instagram, but with a tennis match.
After tennis, it’s straight to her local Starbucks for a piping hot coffee — reportedly a whole milk grande latte with a blueberry muffin.
Lunch is apparently always a “steak and caprese salad without the tomatoes” according to Anna: The Biography by . The $77 meal is always eaten on real plates, never from a takeaway container.
She’s known for her almost military precision: meetings are timed to the minute, and she’s famous for leaving events early — sometimes before the main course is served. If you’re late, you’re out. If you’re early, you’re probably still out.
And then, there’s the hair. That iconic bob isn’t just a style, it’s a commitment. The New York Times reported that Anna gets her hair trimmed every single day by her longtime stylist, John Barrett.
As for her wardrobe, Anna is famously loyal to Chanel and Prada, and she’s been known to wear the same favourite pieces on repeat — because trends are for other people.
Her assistants have said they can set their watches by her movements. The devil, it seems, is in the details.
Anna Wintour’s legacy is a complicated patchwork of innovation, controversy, and pure, unfiltered influence. Whether you loved her, feared her, or just wondered how she kept those sunglasses on indoors, one thing’s certain: fashion will never be quite the same.
Lead image: Getty Images / Vogue
