What Does Anna Wintour Know?

We all have a hill that we’ll gladly die on. My roommate routinely goes on tirades about how no movie should be over 90 minutes (sorry, Scorcese). A lot of people on the internet are currently committed to the hill (read: conspiracy theory) that Kylie Jenner and Timothee Chalamet are a PR stunt engineered by Kris.

I’ve said it once and I’ll say it over and over for the rest of my life: mine is that the Kim and Kanye Vogue cover of September 2014 caused a major vibe shift.


This, to me, is the first cultural domino to fall and we’re still living in its aftermath. It’s the hill I hope they bury me on. So let me explain.

The September issue of Vogue is a big deal. It’s an extra thick, extra coveted issue because it’s usually the highest circulation month and advertisers literally fight — and bribe — for their spots in it. So do models, celebrities, and brands. Therefore, the unveiling of the September cover is always a big deal. In 2014, Vogue took a giant gamble: putting Kim and Kanye on the cover to celebrate their wedding.

These days, a Kim K cover would be a no-brainer — she was just GQ’s Man of the Year, for example, and posed on the cover with a bag of Cheetos — and a Kanye cover would be unfathomable — he’s in Wyoming somewhere, canceled. But in 2014, Kanye was a certified rap royalty and Kim Kardashian was still only known for her reality show and penchant for bandage dresses.

Almost a decade ago now (do you feel old yet?), the cultural landscape was completely different. Rap music, for example, had been popular for years but was only just going from a fringe genre to a welcomed part of the mainstream. So, although Kanye was a household name, he was a surprising choice for the cover. His fashion foray, Yeezy, was still getting its sea legs and not yet the giant it would become. And as for Kim? She was pretty much a joke.

But this Vogue cover changed it all. People were outraged— saying Vogue had lost the plot and that it was going downhill — but Anna Wintour stuck to her guns. She took a risk, made a bet that KimYe would be fashion’s next hottest couple, and, against all odds, she was right.

After that cover, fashion changed. So did culture itself. Slowly but surely, we entered the streetwear and hypebeast era. Ruled by sneakers and sweatsuits, this era embraced a hip-hop-inspired take on fashion that contrasted with the business-casual attire of the late 2000s and the millennial hipster chic of the early 2010s. Supreme became the hottest brand on the market. Sweatpants became acceptable club attire. And meanwhile, KimYe was proving Anna Wintour right one Yeezy ensemble at a time.

Anna’s gamble also foreshadowed how intertwined fashion would become with celebrity culture. These days, front rows of fashion shows are filled with actors, singers, and internet personalities over editors and industry vets. Budding industry darlings make names for themselves by becoming “fashion girls” and partnering with brands like Loewe, Schiaparelli, and Jacquemus. Even Kylie Jenner just launched a fashion line — maybe we’ll see her grace the cover of Vogue next.

But now, Anna has taken yet another risk.

Out of nowhere, just days ago, Vogue Magazine posted a very surprising pair on social media: Amazon billionaire CEO Jeff Bezos and his new wife Lauren Sanchez.

The write-up was even weirder. From comparing Bezos to Iron Man (he wishes) to revealing that Lauren once outbid Kim Kardashian on a dress for $200,000… this Vogue spread felt like a paid advertisement for Jeff Bezos’s mid-life crisis. Don’t get me wrong, I love it when hot girls have post-divorce revenge eras — like Em Rata or even Jeremy Allen White — but Jeff Bezos? We can’t give him the validation.

And I’m not alone in thinking this. Vogue readers were fuming. Just check the comment section or the TikTok video essays. In the court of public opinion, billionaire Bezos is not winning. Some readers asked how much Bezos was shelling out for this profile, while others pointed out that Mackenzie Scott, his ex-wife who has committed to donating her fortune, would have been a better feature.

But I can’t help but wonder: what does Anna Wintour know? Could another vibe shift be imminent? Now that we’re used to seeing celebrities leverage fashion in service of their fashion brand, will we be seeing tech moguls and billionaires do the same? Next thing you know, Elon Musk will be the face of Balenciaga and all the tech kingpins will stop trying to go to space and instead try to score invites to the Met Gala and Vogue World.

If that’s where all this is headed, it’s looking pretty bleak. Not to undermine Anna’s judgment, but in this scenario, I hope she’s wrong.

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