Anna Wintour: The wardrobe of fashion’s high priestess

For 25 years, Anna Wintour has been at the helm of fashion bible, Vogue. But what do the clothes of the aloof style editor tell us about her? Katya Foreman investigates.

Skim along the front row of any major fashion show – a human skyline of sorts – and a handful of silhouettes will always be seen, like cartoon characters that have infiltrated the real world. These shapes include those of Suzy Menkes, fashion editor of the International Herald Tribune with her trademark high-rise quiff; Franca Sozzani, editor-in-chief of Vogue Italia, and her long mermaid locks; Grace Coddington, creative director of Vogue, with her flame-red tresses and finally Anna Wintour, Vogue’s editor-in-chief, who was recently named artistic director of the entire Condé Nast publishing empire. This summer marks the 25th anniversary of Wintour’s reign at Vogue – a period throughout which she has steadfastly sported the same haircut: a perfectly coiffed bob, so thick and fixed it could pass for a wig.

Widely regarded as the most powerful figure in the fashion industry, British-born Wintour, 63, has cleverly crafted a protective helmet with her ’do and ubiquitous shades; the famously aloof editor (nicknamed ‘Nuclear Wintour’) gives the impression that, if she removed her specs, anyone catching her gaze would be instantly turned to stone. Yet despite her icy reputation, Wintour – who made The Guardian’s 50 best-dressed over-50s list this March, is a surprisingly feminine dresser; her signature looks include tweed suits by Oscar de la Renta and Chanel, textured A-line skirts and below-the-knee, sleeveless pencil dresses that show off her tennis-toned arms. (Famously one of Roger Federer’s biggest supporters, she’s said to rise at dawn to spend an hour on the court most mornings.)

Wintour likes colour and bold prints, tempered by sleek cuts and neutral footwear – typically bespoke nude slingbacks by Manolo Blahnik. As for accessories, chunky crystal necklaces are another Wintour wardrobe staple, her modern-day take on pearls, but she is rarely seen carrying a bag (occasionally she’ll clasp a clutch big enough to hold her ever-present BlackBerry). Footage from a 2000 BBC documentary has revealed an androgynous side to the editor, in simple pants and a white polo neck evoking Audrey Hepburn, but she hasn’t been seen wearing trousers to an event in around ten years. She’s also oddly averse to black, fashion’s go-to shade for instant style. A scene in 2009 documentary The September Issue sees Grace Coddington pull a black leather jacket from a rail of clothes and ponder aloud, “I wonder if Anna would like this one?” “Well, it’s black...” someone answers off-camera, to which Coddington replies, “That’s true, I’d be fired for that”, before hanging it back on the rack.

Black mood

In the 2000 BBC special Boss Women: Anna Wintour, the editor is seen previewing a collection by former Yves Saint Laurent creative director Stefano Pilati. “So you’re not really feeling colour, Stefano?” she barks, beadily eyeballing the grey creations being presented for her approval. A defeated-looking Stefano replies, “No, you know, it’s my mood; in winter I never feel so much for colour. It’s more a summer thing for me, frankly...” Narrowing her eyes, Wintour lowers her head disapprovingly, blinks furiously then sighs. It’s a scene mirrored in roman à clef The Devil Wears Prada, where Meryl Streep’s Wintour proxy, Miranda Priestly, damns an entire collection with the merest pursing of her lips, sending a designer into utter despair.

Wintour’s approval is equally seismic, with a nod ensuring considerable success. She restyled Adele between the release of her first and second albums, taking the plus-sized Londoner from frumpy and formless to effortlessly elegant, complementing – if not even enhancing – the 26 million-selling album 21. Wintour’s championing of erstwhile Dior designer John Galliano didn’t end with his on-camera anti-semitic rantings (she’s said to be helping him rebuild his career). And anointing fashion-mad rapper Kanye West helped him sell out an entire order of $120 plain-white APC ‘Hip Hop t-shirts’ in hours online, even after his slashed 'n’ layered 2011 debut catwalk collection was universally slated. (Her fondness for West only goes so far; while his girlfriend, Kim Kardashian, eventually wangled an invite to the ultra-exclusive, Wintour-curated Met Ball last May – to which she wore a widely-ridiculed chintzy Givenchy frock – she is said to be persona non grata to Vogue, as is baby daughter North.) Like West, Wintour also favours fur. The September Issue shows a pelt-wearing Anna being asked by a reporter, “Is there a way to wear fur this winter?” “There’s always a way to wear fur,” she snaps. “Personally, I have it on my back.”

Wintour’s unapologetic fashion approach to her own clothes frequently sees her zero in on key pieces she will then recycle throughout a season – an admirably thrifty act seen as transgressive in the fickle world of fashion. Sporting the same Carolina Herrera floral shift three times in two weeks made headlines. “It is unthinkable that she would make a fashion faux pas. So when Vogue editor Anna Wintour made her third appearance wearing the same dress in the space of a fortnight, observers could only conclude she was making a style statement,” concluded the Daily Telegraph in 2008. There is certainly always method to her dressing. “Each of Anna’s sartorial decisions are deliberate as she decides which trends to promote,” insisted The Huffington Post in a 2009 article entitled Breaking! Anna Wintour Steps Out In Flats.

A game of chess

It’s popular to believe that the fashion world is grandmaster Wintour’s game, with even its most powerful players her pawns, but she is neither as vindictive nor as humourless as this implies. Co-stars Streep and Anne Hathaway have both graced the cover of Vogue since The Devil Wears Prada was released, for instance, and Wintour reportedly even wore the label of the title to a private preview of the film back in 2006.

And of course she’s not infallible. The fashion police happily opened fire on a futuristic silver Chanel gown she wore to the Met Ball in 2008, which went on to top Time’s Top 10 worst outfits of the year. “When the history of modern fashion is written, this will be its Waterloo moment,” said the esteemed magazine, somewhat extravagantly. One could see it as karma for all the designer digs Wintour has made across her career – The September Issue is littered with such asides as “It’s just dreary...” and “It’s not big on ‘hanger appeal’...” – though, in her defence, the Met Ball event was themed around the Costume Institute’s new exhibition, Superheroes: Fashion and Fantasy. Maybe then, as now, she was simply ahead of her time.

Love or loathe her style, Wintour, who makes her living telling other women how to dress, has nailed a look that flatters her physique and features. Her choice of colours, textures and prints hint at a softer side to her character, or at least the desire to convey such a message, and her lack of luggage and barely-there nude footwear give an impression of lightness. You won’t see Wintour with bed hair, worrying about the size of her bottom in a pair of jeans, or scuffing her shoes. The overriding message of her tailored-to-a-t, groomed appearance is that she is sartorial perfection personified, dictating but seldom succumbing to trends.

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