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


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


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


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


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

Related: 5 "Boring" Basics Both Meghan Markle and Anna Wintour Wear


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


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


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


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Style 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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Style Notes: This neckline is beyond gorgeous.


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


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


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


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Style 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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Style Notes: Stripes and stripes are foolproof. Fact. 


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Style 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. 

Related: Anna Wintour's Power Bob Suits These Face Shapes


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


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Style 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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Style 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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Style 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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Style 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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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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Style 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.

Consider Anna Wintour's word as gospel? Then you'll definitely want to find out her she considers the biggest job interview faux pas to be

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.