The 20 Best Anna Wintour Outfits That You Probably Haven't Seen Until Now

by Danielle Naer and Kelsey Stewart
Originally Published: 

Anna Wintour's style file has been carefully documented over the last 40 years. Since becoming head editrix of American Vogue in 1988, the now-mogul has layered up (fur coats, high-neck frocks and tall boots) and down (slinky sequin dresses and strap-y heels) for just about every occasion. Though known for her consistency, it may come as a surprise that the best Anna Wintour outfits are actually super different from one decade to the next. Her now-polarizing aesthetic has changed significantly since her early years, which sported all the exuberance of a young editor in the heyday of her career.

The early '90s, for example, were laden with youthful silhouettes including leggings and crewnecks, mesh cut-out tops and coogi skirt-suits, which made what followed all the more surprising. Her signature style as we know it — colorful, printed frocks, flanked by shadowy Chanel frames and criss-crossed Manolo Blahnik's (which are remade from a mold of her foot every season) — was solidified much later. As is true in fashion and life, it's all about the journey; and Wintour's is no exception.

Ahead, you'll find a sequential round-up of AW's very best ensembles, from Met Gala red (or, sometimes pink) carpets to far-flung fashion weeks over the years. Be sure to shop similar standout pieces, to ensure your style is just as timeless.

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Ultra-Bright (1990)

Wintour knows a thing or two about a statement coat. Her Chanel bright yellow sequin jacket she wore at an Armani dinner in 1990 could probably be spotted blocks away. Here's the good thing: You can currently snag the piece on Farfetch (but act fast!).

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Rainbow Sequins (1990)

Rainbow sequin dress? You bet Wintour has rocked it. Try a modern take on her 1990 number with Markarian's Tidy Tips Striped Sequin Dress.

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Dark Color Palette (1988)

Wintour's rust and black ensemble at a costume exhibit in 1988 was more on the subtle side for the style icon, but chic nonetheless.

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Orange + Pinstripes (1996)

Pairing together a bright orange silk top and pinstripe suit might not first come to mind, however, Wintour proves its worth giving a go — as shown by her look at 7th on Sixth fashion show in 1996.

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Animal Print Gown (1997)

Wintour wasn't shy when it came to playing around with funky animal prints, as exhibited above. The EIC wore a luxe fitted leopard print maxi dress to the PEN American Center Gala Honors in 1997.

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Printed Set (1990)

If anyone can pull off a wacky, vivid print, it's Wintour. During a Paris Haute Couture Fashion Show in 1990, she finished off her pattern set with chunky pearl necklaces and simple slide-on sandals.

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Little Black Dress (1989)

The little black dress is a staple piece in any woman's wardrobe. As displayed by Wintour, a printed crop blazer can dress up any simple minidress — as will, of course, a quilted Chanel Bag.

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Spaghetti-Strapped Sequins (1990)

Ms. Wintour was all about sequins in the early '90s, and the Paris Haute Couture Cocktail Party was no exception. She and Karl Lagerfeld are pictured here at the Plaza Hotel in NYC.

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Mesh Cutout Top (1991)

Wintour channels the rasta trend of the '90s with this pleated circle skirt, finishing the look with a mesh cutout bodysuit that's just as chic today.

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Playful Crewneck (1993)

This whimsy-filled sweatshirt floats the '80s workout gear trend, calling on lace-hemmed bubblegum pink leggings, ballet flats, and a waist-tying sweater for added nostalgia.

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Contrasting Fur Coat (1994)

Wintour layered her two-toned furry coat over a silk slip dress for the Met's Annual Costume Institute Benefit in New York City in 1994 (which years later would be renamed, "The Met Gala").

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Tonal Dressing (1996)

Tonal dressing is indubitably hard to master, but Wintour's semi-casual look makes it simple. Pair a textured overcoat with a simple ribbed tee and pressed satin trousers — and be sure to keep it all in the same color family.

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Orange Silk (2001)

For the premiere of Moulin Rouge! in 2001, Wintour wrapped a fur pelt around the neck of her electric orange halter dress, and finished the look with metallic, pointed-toe pumps.

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Skinny Jeans (2001)

The UK-born editor indulged in this all-American look for the VH1/Vogue Fashion Awards in NYC, proving once and for all that skinny jeans can be red carpet appropriate, too.

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Utilitarian Shirtdress (2005)

A very sun-kissed AW wore this embroidered utilitarian dress along the front rows of Fashion Week in 2005, along with her famous Manolo's.

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Muted Tweed (2011)

For Chanel's Ready-to-wear Spring/Summer 2012 show, Wintour's tweed look was all too appropriate, wearing an asymmetrical double-breasted blazer that epitomized the early '10s. For the 2021 version, shop Balmain's olive green fringe iteration.

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Snakeskin Trench (2012)

In Milan, Wintour wore this reptilian look for Giorgio Armani's Autumn/Winter 2012 show — and the piece has reappeared in her wardrobe as recently as this year.

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Embellished Silk (2016)

Wintour's embellished Prada qipao dress made a huge statement at Glamour's Women of the Year awards in 2016. While the frock itself is totally unavailable, Onīrik's rust-colored frock is a more casual approach to the silhouette.

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Bright Florals (2019)

Wintour has been a long-time tennis fan, and there are dozens of stylish US Open appearances to show for it. Here, she donned one of her favorite staple prints — bright florals, along with a cobra baby blue shoulder bag.

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Ostrich Feathers (2019)

Last but not least, we have Wintour's 2019 Met Gala look, which was the last that Karl Lagerfeld would architect for the occasion before his passing. Quality Ostrich feather wares are well worth the price tag, and Maison Margiela creates the perfect pink poncho to get the look.

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