Anna Wintour's Flawless Fashion Week Looks From 1994 to Literally Yesterday
As all eyes turn to the street style elite to see their eccentric fashion week wares, there’s another fashion force whose style, albeit more understated, we never fail to be impressed by: Anna Wintour. Far from being a slave to the trends, the editor in chief of Vogue U.S. —a position she's held since 1988—is known for her classic style. Printed dresses with coordinating coats are considered her uniform, as is her signature sleek bob and, of course, those Chanel sunglasses. It’s a look that’s served her well for over 20 years, and one we’ve come to expect throughout the course of fashion month.
At every single show, there’s a front-row seat specifically reserved for Anna in the mere hope she’ll make an appearance. And when she does, which to her credit is very frequently, we can count on her to look impossibly chic and ladylike. Needless to say, her decades of fashion week dedication shouldn’t go unnoticed, which is why we’ve decided to document her best-ever front-row looks, from the first snapped sighting of her sitting pride of place in 1994, all the way up to, well, yesterday. You know what to do—keep scrolling to see Anna Wintour’s fashion week outfits.

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Getty ImagesStyle Notes: You're going to hear a lot of talk about printed dresses, cross-strap sandals and layered necklaces in this article. And, true to form, that's exactly what Anna chose to don to New York Fashion Week in September 2019.

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Getty ImagesStyle Notes: Anna masterfully coordinates the colour of the gemstones in her necklace to that of her dress.

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Getty ImagesStyle Notes: It takes guts to clash geometric and snake prints, but for Anna, it's a breeze.

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Getty ImagesStyle Notes: Taking to the streets of Paris in February 2019 wearing a bottle-green leather coat, which enhances the vivid green in her dress beautifully.

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Getty ImagesStyle Notes: Snake isn't the only animal motif in Anna's wardrobe repertoire. She's also a big fan of faux-leopard and fawn prints.

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Getty ImagesStyle Notes: Leopard and snake prints in the same ensemble? And it works? Now you're just showing off, Anna.

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Getty ImagesStyle Notes: Even Anna couldn't resist grabbing a scarf as she dashed out the door on a chilly day during New York Fashion Week in February 2019.

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Getty ImagesStyle Notes: Chanel bouclé twin sets were practically created for the EIC…

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Getty ImagesStyle Notes: Anna is a big fan of coloured leather, as her burgundy boots and coat prove. They make for the perfect accompaniment to her bold dress, which she donned during Paris Fashion Week in September 2019. But, of course, she already knew that.

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Getty ImagesStyle Notes: Yes, Anna does rewear her clothes and shoes. Case in point? The previous slide.

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Getty ImagesStyle Notes: And again, only this time she's paired them with a graphic, '60s-style floral print dress. Parfait.

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Getty ImagesStyle Notes: Anna seamlessly blends her striped and zebra pieces by sticking to a similar colour palette. We love the clash of her yellow shoes against the classic white and navy.

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Getty ImagesStyle Notes: Anna defaults back to a floral and snake-print combination during New York Fashion Week in September 2018. Well, if it ain't broke…

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Getty ImagesStyle Notes: Anna, we'll gladly take this checked trench off your hands.

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Getty ImagesStyle Notes: The check-and–floral-print mix-up we regularly come to rely on was practically invented by Anna.

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Getty ImagesStyle Notes: We don't know what we love more—Anna's toffee-hued boots, or the mirror-print dress she wore to attend the Richard Quinn show during London Fashion Week in February 2018.

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Getty ImagesStyle Notes: This neckline is beyond gorgeous.

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Getty ImagesStyle Notes: It's evident that evergreen is one of Anna's favourite shades to wear, as is tan and burgundy.

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Getty ImagesStyle Notes: Tie-dye and tartan is a print clash we never thought out trying for ourselves… until now that is.

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Getty ImagesStyle Notes: We're still weeping over not getting our hands on this beautiful embroidered Stella McCartney coat, which Anna wore to take in the designer's Paris Fashion Week show in March 2016.

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Getty ImagesStyle Notes: Military coats never fail to look chic. Anna knows this all too well.

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Getty ImagesStyle Notes: The colour combination of poppy red and denim blue couldn't be more beautiful. This look from Lanvin's Paris Fashion Week September 2014 show is one of our all-time Anna favourites.

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Getty ImagesStyle Notes: Stripes and stripes are foolproof. Fact.

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Getty ImagesStyle Notes: Anna often relies on Altuzarra to outfit her fashion week wardrobe—and here she is wearing a printed shirtdress by the designer at New York Fashion Week in September 2012.

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Getty ImagesStyle Notes: Anna wears a statement coat with leather knee-high boots ahead of Louis Vuitton's September 2012 Paris Fashion Week show.

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Getty ImagesStyle Notes: Animal print and bows? Anna pulls out all the stops for her appearance at the Giorgio Armani Milan Fashion Week show in September 2009.

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Getty ImagesStyle Notes: Anna was wearing slip skirts well before they took off in 2019—during Rag & Bone's New York Fashion Week show in September 2009, to be precise.

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Getty ImagesStyle Notes: Anna knows you can never go wrong with a white shirt, midi skirt and a Starbucks.

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Getty ImagesStyle Notes: With empty rows behind her, Anna takes a moment to kick back ahead of Rag & Bone's September 2005 catwalk show.

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Getty ImagesStyle Notes: The jumper, the skirt, the sandals… Anna's 2003 New York Fashion Week look is one we'd gladly wear today.

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Getty ImagesStyle Notes: Anna in jeans? Much like the rest of us, the Western trend serves as Anna's guilty pleasure. This look, which she wore to Sean John's New York Fashion Week show in 2003, is one of her best.

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Getty ImagesStyle Notes: Anna arrives at Diane von Furstenberg's 2002 catwalk show in NYC in a very on-trend all-white outfit.

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Getty Images:Style Notes: Anna's love of faux fur goes all the way back to 2001, when she wore head-to-toe Carolina Herrera to the designer's New York Fashion Week show.

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Getty ImagesStyle Notes: The first documented photograph of Anna at a fashion week show (that we could track down, at least) is from 1994, where her blouse was as shiny as her hair. Perfection.
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