Anna Wintour's Earliest Style Moments Are Just Golden

Anna Wintour's young style was surprisingly bold. When the powerful editor was rising to prominence and becoming a FROW regular, Wintour's business attire was put to good use. Her evening choices were glitzier than one might think (hello, rainbow dress) while day-to-day office looks remained on par with today's ladylike style (Chanel skirt suits and an ever-present string of necklaces).

The bob has always been in position. Sunglasses crept in during the '90s, and her trusty Manolo Blahniks were a fixture in even some of the earliest outfit snaps. Despite some high-octane '80s combos, this woman has always known what suits her when it comes to shapes, designers and colours. Go through the gallery to see a young Anna Wintour's fashion looks in action.


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Style Notes: Just when you've downsized to micro-sunnies, along comes this impressive jumbo, chain-embellished pair on Anna Wintour circa '94. Also—orange satin shirt… Who knew?


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Style Notes: Forever a fan of the chunky jewel necklace, Anna found the perfect way to flourish her corseted LBD in 1989.


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Style Notes: On an evening in 1990, Anna Wintour wore the party dress trend that's taking over in 2017—rainbow sequins.


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Style Notes: Ninety-four's furry coat + satin slip dress + mules = something Bella Hadid would totally wear today.


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Style Notes: Who knew Anna Wintour loved a jazzy print quite so much? She chose this vibrant two-piece for a Paris Haute Couture Fashion Week party in 1990.


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Style Notes: Sometimes nothing is better than a red slip dress and tan Manolos.


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Style Notes: We'd never put Anna Wintour down as a fan of sparkle, but here she is in the '90s proving otherwise.


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Style Notes: This feels very right for the comeback Versace is experiencing with its S/S 18 collection.


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Style Notes: Here it is—the classic bouclé skirt suit. Worn, as per usual, with nude shoes, sunnies and a string of necklaces.


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Style Notes: Red! Yellow! Three lots of satin! Anna wasn't messing around with this bold look, and it's possibly our favourite of all.


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Style Notes: Pale pink knitwear is our current obsession, but Wintour did it justice way back when with a pastel coat and high-shine trousers.


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Style Notes: Power shoulders weren't Anna's invention, but she certainly knows how to pull them off—a sleek miniskirt does the balancing trick.


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Style Notes: Long before athleisure came along Anna was doing oversize skiwear.


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Style Notes: Such a perfect fluorescent yellow dress. How very S/S 18 of you, Anna. 


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Style Notes: There's only one bad thing about this outfit: KiraKira+ didn't exist (or Instagram, for that matter) for it to be adored all over social media.


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Style Notes: So elegant.


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Style Notes: This exceptional leopard-print coat is anything but mumsy, even if she is a mum. 


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Style Notes: We're pretty keen on satin skirts right now, but Wintour knows that pairing one with a black top and a quilted bag is the way to go. 

Next up, the Anna Wintour quotes we can't get enough of.

This post was originally published at an earlier date and has since been updated by Elinor Block.

Hannah Almassi
Editor in Chief

Hannah Almassi is the Editor in Chief of Who What Wear UK. Hannah has been part of the the Who What Wear brand since 2015, when she was headhunted to launch the UK sister site and social channels, implement a localised content strategy and build out the editorial team. She joined following a seven-year tenure at Grazia magazine, where she led front-of-book news, fashion features and shopping specials as fashion news and features editor. With experience in both print and digital across fashion and beauty, Hannah has over 16 years in the field as a journalist, editor, content strategist and brand consultant. Hannah has interviewed industry heavyweights such as designers including Marc Jacobs and Jonathan Anderson through to arbiters of taste including Katie Grand and Anna Dello Russo. A skilled moderator and lecturer specialising in the shift to digital media and e-commerce, Hannah’s opinion and work has been sought by the likes of CNBC, BBC, The Sunday Times Style, The Times, The Telegraph and, among many others. Hannah is often called upon for her take on trends, becoming known as a person with their finger of the pulse of what’s happening in the fashion space for stylish Brits. Hannah currently resides in Eastbourne with her photographer husband, incredibly busy son and highly Instagrammable cat.