Feared and revered, Anna Wintour is at the helm of global fashion.
The Vogue editor is fashion’s sphinx, sitting in her bob and sunglasses like she’s guarding the gates of chic. Dictating what is in and who’s tragically out is her bread and butter, in turn keeping the trends cycle neatly ticking over.
Anna’s career is legendary in the fashion industry, spanning more than four decades. Born in London in 1949, she began her career in journalism at Harper’s & Queen before moving to New York, where she held editorial positions at Harper’s Bazaar and Viva. Her vision and ambition quickly set her apart, and she climbed the ranks to become editor-in-chief of British Vogue in 1985. Just three years later, she took over as editor-in-chief of Vogue in the United States, a role she’s famously held since 1988.
© GettyHer tenure transformed Vogue into a powerhouse that defines global fashion. She introduced a fresh editorial style, combining high fashion with celebrity allure and streetwear, while championing the careers of now-famous designers like Marc Jacobs and John Galliano. Beyond her work at the publication, Wintour became artistic director of Condé Nast in 2013, expanding her influence across all the company’s publications.
Known for her cool, reserved demeanour, she’s both celebrated and criticised as the ‘Ice Queen’ of fashion. Her annual Met Gala has become fashion’s most exclusive event, cementing her role as a cultural force. Through Anna’s vision, Vogue remains at the forefront, catalysing trends and shaping the industry.
To celebrate her 75th birthday, we’re taking a look back at Anna’s ten best looks to date.
Anna Wintour’s 10 most stylish outfits ever:
© Ron GalellaDisco Mini Dress
In 1990, the Scorpio Queen served up Studio 54 glamour as she attended a New York Ballet gala at the New York State Theater. The journalist wore a glittering silver dress featuring a mini silhouette and long sleeves.
Mesmeric Marc Jacobs
The very same year, the Vogue editor-to-be attended the Book Party for Holy Terror: Andy Warhol Close Up alongside Bianca Jagger. She glimmered in Marc Jacobs, sporting another disco-ready look hailing from the American fashion designer’s archive.
Pink Power
1990 proved to be a particularly fruitful year for Anna’s wardrobe. The London native joined John Galliano to attend the Council of Fashion Designers of America’s awards ceremony, with the writer opting for a magenta slip dress complete with floral embroidery.
© Rose HartmanFur Cape
One of fashion’s most eyeballed fall-outs was between the late André Leon Talley and the Vogue matriarch. Pictured together here, Anna dazzled in a lavish fur-cut cape, layered over an embroidered gown, while her then-editor-in-chief commanded attention in a gold-hued brocade evening coat.
© WWDPlumes O’Plenty
Joined by Tom Ford at the 2003 MET Gala, the style veteran glimmered in a bridal dress complete with fluid silk material and a brilliant feathered shawl that perched on her shoulders.
© Karwai TangA Note On Camp
For the 2019 Met Gala titled ‘Camp: Notes on Fashion,’ Anna looked to Chanel’s former creative director Karl Lagerfeld to create a frothy pink look crafted from Maribou feathers, layered over a beaded floral gown. The look ended up as an homage to the designer, who passed away that year.
© Dimitrios KambourisPrada Panache
Anna graced the red carpet at the GQ’s Global Creativity Awards 2023 in New York City, debuting a silky look courtesy of Prada. The longline dress featured contrasting pearlescent panels, long sleeves and floral print detailing.
© Christian VierigPlaid Persuasion
Spotted outside the Alaia show back in July 2023, Anna let her penchant for plaid be known in a wine red and ivory checked piece. The striking number adopted her go-to silhouette, ankle-grazing with long sleeves in a print Burberry would approve of.
© Jacopo RauleValentino Florals
Anna pre-empted this season’s captivation with burgundy hues as she graced the Valentino Womenswear Spring/Summer 2024 during Paris Fashion Week in a silk floral dress. The editor loved this particular number so much she even has it in forest green. Versatility at its finest.
© GettyTulip Enchantment
The 2024 Met Gala celebrating ‘Sleeping Beauties: Reawakening Fashion,’ saw swathes of familiar faces ascend the staircase, including host and MET matriarch Anna. Designed by LOEWE’s Jonathan Anderson, Anna’s look features a tulip-strewn black cloak, layered over a white dress.
