The Iconic Bob in Sunglasses: Anna Wintour’s Legacy
The bob, the sunglasses, the barely-there smile. Equal parts mystique symbol and fashion icon. For over three decades, Anna Wintour hasn't just directed the pages of Vogue… She dictated what the world should wear and why we should care. Say what you want, but when Anna speaks (or even just raises an eyebrow), the fashion industry listens.
From London Rebellion to Manhattan Power: Inside the Wintour Legacy
Anna Wintour was born in London in 1949, into a world where storytelling and influence were daily currency. Her father, Charles Wintour, was a prominent editor of the Evening Standard, and her household was steeped in media, politics, and sharp opinion. Her mother, Eleanor Wintour, brought a quiet intellect and artistic sensibility to the family, offering a subtle but lasting influence, to shape independence and cultural awareness. From an early age, Anna was exposed to the mechanics of publishing - how headlines were crafted, how power moved through words and how image could be as persuasive as fact. But even then, she wasn’t one to follow expectations and she wasted little time blending in. Anna couldn't stand school uniforms, she adjusted hemlines and curated her own look before most teens knew what “style” even meant. At 16, she dropped out of school and enrolled in a fashion training program at Harrods, while also working at Biba, a now-legendary boutique in London. It wasn’t academia that shaped her, it was the street, the style, the rhythm of a city in cultural bloom. While her peers chased grades, Wintour was already observing silhouettes, editing looks and building the instincts that would define her career. Her early rebellion wasn’t careless, she just wanted to edit the world around her. Her early career began in the 70s at Harper’s & Queen before she made the move across the Atlantic. New York needed her, and she hopped across publications like Harper’s Bazaar, always with an eye for what was next. By the time she landed Editor-in-Chief of Vogue US in 1988, she wasn’t there to maintain tradition. Her first Vogue cover? It featured a model in a Lacroix couture top and $50 Guess jeans. The fashion world gasped. Her audacity. Anna wasn’t here for approval, she was here to redefine relevance. Her aesthetic wasn’t just accidental, it was directional. Wintour had spoken and she had no patience for the fussy, the outdated, or the simple pretty. She wanted now, next and necessary. Under her reign, Vogue stopped being a fashion magazine and became the fashion oracle. Wintour turned it into a mirror for culture. Sharp, provocative and unafraid to mix politics with Prada.
The Power of Wintour’s Eye: Tastemaker-in-Chief
Anna Wintour has always had a sixth sense for spotting talent, often before anyone else dared to look. She’s been behind the rise of designers, catapulted models, photographers, and stylists into global stardom. From John Galliano’s early collections to Marc Jacobs’ most recent shows, when she believes in a designer, she doesn’t just cover them; she connects them to the people, platforms and investors that build legacies. Her support is rare, quiet, and never performative. In fashion, that kind of loyalty is more valuable than gold. She put celebrities on covers when it was still considered taboo and while others in the fashion industry struggle to keep up with cultural shifts, Anna has a way of staying ten steps ahead, without ever breaking her signature poker face. Putting Madonna, Gwyneth Paltrow or Serena Williams on the cover wasn’t just bold, it was disruptive. Critics called it commercial. Anna called it strategic. She understood that clothes alone weren’t enough; the public craved a story, a persona, an icon. While the industry has issues with confronting its lack of diversity and inclusion, Wintour has - admittedly late, but publicly - pushed for change and acknowledged missteps.
Discipline in Designer Heels
Behind the scenes, Wintour runs on precision. Her routine is legendary: early morning matches at 5:45 are her type of meditation, daily bob blowouts and a desk cleared of clutter by mid-morning, is Annas normal way to go. Friends and longtime collaborators describe her as loyal, deeply private and more intuitive than cold. Anna Wintour has always balanced her high-profile career with a grounded personal life. Her family remains off-limits to the press, protected by the same unshakable poise she brings to the front row. She has two children from her first marriage to child psychiatrist David Shaffer, whom she married in 1984 and divorced in 1999. Her son Charles is a political editor in major publications including The New York Times, while her daughter Katherine has worked as a television producer on shows like Glee and Scream Queens. Unlike their mother, both have largely avoided the spotlight and only occasionally appeared beside her at the Met Gala. After a decade-long relationship, which ended quietly around 2020, Wintour has remained single. True to her Scorpio nature, she keeps her personal life guarded, her circle tight, and her emotions well beneath the surface. Family remains sacred and discreetly protected by the same unshakable poise she brings to every front row. Scorpios are known for their intensity, privacy and revolutionary presence, qualities that mirror the famously mysterious and powerful figure behind the Vogue empire. In her free time, Wintour is a devoted tennis enthusiast; she plays religiously and attends Wimbledon with the same focus she brings to the front row. Often spotted courtside in Celine, cheering with collected intensity. Despite her unshakeable routine, those who stay close to her say her power doesn’t lie in volume, but in attention. She may be the last person to overshare, but Anna is the first to sense when you need help. She remembers the personal details most others forget. She’s also famously punctual, responds to emails before sunrise, and has been known to walk out of shows that start late. A silent protest wrapped in Chanel tweed. She is as regimented as she is stylish, rarely deviating from her core wardrobe of printed midi-length sheath dresses, tailored jackets and pointy Manolo Blahnik heels in neutral tones or python skin. The silhouettes are always sharp, elegant and unmistakably her: fitted and feminine. She rarely wears black, preferring color and texture like florals, metallics or bold geometric prints from designers like Oscar de la Renta, Tom Ford and Prada. Her oversized Chanel sunglasses are non-negotiable. She wears them indoors, outdoors, front row, backstage, on Zoom. She doesn’t accessorize much. No statement earrings. No trending handbags. She knows what she likes and that discipline is not at all a trendy aesthetic, it's her character and the foundation of her power.
The Impact Doesn’t Step Down
Beyond the Pages, there is more than just the fashion figurehead. She’s a cultural strategist. As Chief Content Officer of Condé Nast and, until recently, Global Editorial Director of Vogue, she has overseen one of the most powerful editorial empires in modern media. But in June 2025, the whispers became headlines: Anna Wintour is stepping down from Vogue. The announcement sent a shockwave through the fashion world. For some, it marked the end of an era. For others, it sparked one burning question: Who on earth could possibly fill those pointy heels? But don’t mistake her departure for retirement, Anna doesn’t just fade away. You’re still reading the stories she shaped, still wearing the trends she legitimized and watching the designers she anointed. From the rise and fall of supermodels, from minimalism to maximalism and back again, Wintour’s editorial fingerprint is on every era. She’s turned covers into careers, designers into legends, and the Met Gala into a cultural institution. No one has done it like Anna and even as she steps down, her influence isn’t going anywhere. It's sewn into the soul of fashion history.
by Lareen Lareen Roth-Behrendt 
