Anna Wintour didn’t just walk into Vogue in 1988. The British editor kicked the doors open. Her first move as editor-in-chief? Putting jeans on the cover. Not just any jeans, but stonewashed Guess jeans paired with a flashy $10,000 Christian Lacroix jacket.
The 1988 cover was a signal flare. Michaela Bercu, the Israeli model, didn’t stare down the camera in a perfect studio pose. She was outside, wind in her hair, looking off-frame, natural and strong. This cover broke the rules of high fashion, and it did it without saying a word.
Until that moment, Vogue covers stuck to a rigid formula. Studio lighting, polished poses, couture from head to toe. Wintour tossed that out.
Spotlight Time / IG / Some critics of the time thought that Anna Wintour’s 1988 Vogue cover was a mistake!
The industry didn’t know what to make of it at first. Jeans on Vogue? Some critics thought it was a mistake. Others were thrilled. Either way, no one ignored it. That reaction was pure Wintour. She knew how to stir the pot and make it look good doing it.
Anna Wintour wanted Vogue to be more than a glossy magazine. She wanted it to reflect real life, real people, and real style. That first cover said so without spelling it out. The message? Fashion belongs to everyone.
In the years that followed, she doubled down on that approach. Covers started showing celebrities, not just models. She pulled in pop culture, politics, and tech. Madonna, Michelle Obama, and even Kim Kardashian all landed spots on the cover. Wintour made Vogue feel current, not stuck in the past.
She also opened doors. Diversity became more than a buzzword. Naomi Campbell landed her first Vogue cover in 1989. That might not seem like much now, but back then, it was groundbreaking. Wintour didn’t just nod to change. She pushed it forward.
Wintour Steps Down After 37 Years!
Fast-forward nearly four decades, and her impact is everywhere. Anna Wintour stepped down as American Vogue’s editor-in-chief on June 26, 2025. That sentence alone is historic. She held the job for 37 years, longer than many readers have been alive. But she is not out. She still runs the show globally, shaping content across Condé Nast’s empire.
The new person in her old chair won’t carry the same title. “Head of Editorial Content” is the label now, reflecting a wider, digital-first focus. But the job? Still massive. Still shaped by Wintour’s blueprint.
Wintour / IG / After 37 years as the editor-in-chief of Vogue, Anna Wintour, now 75, has officially stepped down.
When people talk about legacy, they often mention trends or famous moments. But Wintour’s real legacy is her vision. She knew how to read the room and the future.
Think about how fashion lives today. TikTok trends go viral overnight. Vintage jeans and luxury jackets? Everywhere. Mixing high and low is a standard now. That idea started on a Vogue cover under Anna Wintour’s rule.
Even now, her touch is felt. Editorial decisions, global campaigns, and cultural coverage all carry her influence. And while she is no longer at the helm of American Vogue, the playbook is hers. Jeans on a couture cover wasn’t a gimmick. It was a promise. Fashion would never be boring again.
Wintour reshaped what fashion journalism could be. She turned a print magazine into a cultural force and made it okay for fashion to be weird, loud, and real.