Anna Wintour's Flawless Fashion Week Looks From 1994 to Literally Yesterday

As all eyes turn to the street style elite for their eccentric fashion week wares, there’s another fashion force whose style, albeit more understated, never fails to impress: Anna Wintour. Far from being a slave to the trends, the editor in chief of Vogue—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. 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.

Anna Wintour Fashion Week Outfits: Anna Wintour in a printed dress and statement necklaces

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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. 

Anna Wintour Fashion Week Outfits:Anna masterfully coordinates the colour of the gemstones in her necklace to that of her dress.

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

Anna Wintour Fashion Week Outfits: It takes guts to clash geometric and snake prints but for Anna, it's a breeze.

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

Anna Wintour Fashion Week Outfits: Taking to the streets of Paris in February 2019 wearing a bottle green leather coat

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

Anna Wintour Fashion Week Outfits: Snake isn't the only animal motif in Anna's wardrobe repertoire

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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. 

Anna Wintour Fashion Week Outfits: Leopard and snake prints in the same ensemble? And it works? Now you're just showing off, Anna...

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

Anna Wintour Fashion Week Outfits: Even Anna couldn't resist grabbing a scarf as she dashed out the door on a chilly day

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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. 

Anna Wintour Fashion Week Outfits: Chanel bouclé twin-sets were practically created for the EiC...

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

Anna Wintour Fashion Week Outfits: Anna is a big fan of coloured leather, as her burgundy boots and coat prove

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

Anna Wintour Fashion Week Outfits: Yes, Anna does rewear her clothes and shoes. Case in point—the previous slide.

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

Anna Wintour Fashion Week Outfits: Anna wears a graphic, '60s-style floral print dress.

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

Anna Wintour Fashion Week Outfits: Anna seamlessly blends her striped and zebra pieces by sticking to a similar colour palette.

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

Anna Wintour Fashion Week Outfits: Anna defaults back to a floral and snake print combination

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

Anna Wintour Fashion Week Outfits: Anna, we'll gladly take this checked trench off your hands

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

Anna Wintour Fashion Week Outfits: The check and floral print mix-up was practically invented by Anna.

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Style Notes: The check-and-floral mix we've come to rely on was practically invented by Anna.

Anna Wintour Fashion Week Outfits:  We don't know what we love more—Anna's toffee-hued boots, or the mirror-print dress

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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. 

Anna Wintour Fashion Week Outfits: Anna wears a bouclé dress wth a funnel zip neckline

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Style Notes: This neckline is beyond gorgeous.

Anna Wintour Fashion Week Outfits: It's evident that evergreen is one of Anna's favourite shades to wear,

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

Anna Wintour Fashion Week Outfits: 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: Tie-dye and tartan are a print clash we never thought about trying for ourselves—until now that is. 

Anna Wintour Fashion Week Outfits: 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: 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. 

Anna Wintour Fashion Week Outfits: Military coats never fail to look chic—Anna knows this all too well.

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

Anna Wintour Fashion Week Outfits: The colour combination of poppy red and denim blue couldn't be more beautiful.

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Style Notes: The color 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 favorites. 

Anna Wintour Fashion Week Outfits: Stripes and stripes are foolproof. Fact.

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Style Notes: Stripes and stripes are foolproof. Fact. 

Anna Wintour Fashion Week Outfits: Anna often relies on Altuzarra to outfit her Fashion Week wardrobe

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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. 

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

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

Anna Wintour Fashion Week Outfits: 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 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. 

Anna Wintour Fashion Week Outfits: Anna knows you can never go wrong with a white shirt, midi skirt, and a Starbucks.

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

Anna Wintour Fashion Week Outfits: 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: With empty rows behind her, Anna takes a moment to kick back ahead of Rag & Bone's September 2005 show. 

Anna Wintour Fashion Week Outfits: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: The sweater, the skirt, the sandals… Anna's 2003 New York Fashion Week look is one we'd gladly wear today. 

Anna Wintour Fashion Week Outfits: Anna in jeans? Much like the rest of us, the western trend serves as Anna's guilty pleasure.

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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.

Anna Wintour Fashion Week Outfits: 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 arrives at Diane von Furstenberg's 2002 show in NYC in a very on-trend all-white outfit. 

Anna Wintour Fashion Week Outfits: 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: 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. 

Anna Wintour Fashion Week Outfits: 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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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.

This post originally appeared on Who What Wear UK.

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