Anna Wintour ran Vogue for 37 years. Thatβs longer than most people have kept a phone number. Or a therapist. Or, letβs be honest, a commitment of any kind. She shaped global fashion, redefined the front row, and made the Met Gala what it is today.
But her legacy isnβt just about influence; itβs also about control. Sheβs been called powerful, brilliant, impossible to read... and also elitist, exclusionary, and out of touch. Under her reign, Vogue set impossible standards for who gets to be seen as "stylish" and who doesnβt.
Still, whether you admired her, feared her, or both, Anna Wintour wasnβt just part of the fashion system. For nearly four decades, she was the system. But now that sheβs stepping down, I want to talk about the bob. And the sunglasses. And the floral dresses. And the coats so sharp they could cut through awkward small talk.
Because while everything in fashion changedβdesigners, trends, silhouettes, even the industry itselfβAnnaβs look didn't. Not once. Not even a little.
She wore the same uniform with military precision for decades. Not to fit in, not to follow trends, but to become something bigger than a person. She became a human logo. And somehow, that made her even scarier (and cooler). Letβs break it down.
1. The bob that could withhold eye contact and approvals.
2. Sunglasses everywhere, because feelings are optional.
Translation: she wasnβt hiding her eyes; she was hiding herΒ reactions. Thatβs next-level emotional control. She turned a pair of Chanel shades into a power move.
Sure, there have been aΒ fewΒ rare sightings of her without themβlike, literal minutes where we caught a glimpse of her bare-eyed. But even at those same events, she'd usually pop back up with the sunglasses back on, like she remembered she had a legacy to protect.
Honestly? I kind of want to try it next time Iβm at an event I hate.
3. Florals for Spring? Groundbreaking. Florals forever? Unstoppable.
4. Coats built for silent judgment.
5. The Sit. You know the one.
There are a lot of powerful people in fashion. But none of them are instantly recognizable from the back of a blurry runway photo like Anna is. She is more of a silhouette that means: βFashionβs about to begin.β You can dress up as her for Halloween and everyone will get it.
She doesnβt just have a look, sheβs built a whole myth around it. And the wild part? While everyone else is busy reinventing themselves every season, Annaβs out here saying, βNah, Iβm good,β and still running the entire industry. She doesnβt blink, she doesnβt switch it up. Instead, she doubles down.
And thatβs kind of the thing; she was the establishment. The rulebook. The velvet rope. While her influence shaped fashion globally, it also reinforced the same gatekeeping that kept it feeling closed off to anyone who didnβt fit a very narrow idea of beauty.
Sure, part of that comes with running a legacy title like Vogue, and even CondΓ© Nast in the later years, for as long as she did. But itβs also fair to ask: how many fresh voices, diverse stories, or everyday bodies were kept out while that legendary bob held court in the front row?
Between 2000 and 2005, Vogue put 81 models on its covers, and only three of them were Black, according to a study by The Pudding. Now thatβs not a great look.
In 2020, a New York Times report on CondΓ© Nast revealed the frustration of former Black employees, many of whom said they faced βignorance and lazy stereotypingβ from white editors whenever Black culture was on the table.
And the criticism hasnβt stopped at Vogue US. In 2022, British Vogue ran a cover featuring nine models from Africa, and still got dragged. All the models had Western-style hair, and their skin appeared digitally darkened. Many saw it not as a celebration of Black beauty, but as a filtered, flattened version of it, designed for the gaze of a very white, very global fashion industry.
Sheβs officially announced her retirement now. But the image she's created? Thatβs going to outlive us all. The bob? Still undefeated. The sunglasses? Probably still on.
But now that sheβs stepped down, thereβs a bigger question hanging in the air: does fashion need another Anna? Someone just as precise, just as powerful? Or is this the moment Vogue finally rethinks who gets to sit in that editorial seat and what the next era should actually look like?
