17 Throwback Anna Wintour Photos You Haven't Seen

There are certain fashion industry icons that the world is fascinated by (or obsessed with, depending on how you look at it), and no one has held our attention more over the past several decades than the incomparable Anna Wintour. Perhaps it's due to the wildly popular and critically acclaimed The September Issue or simply the allure of Vogue magazine. Whatever the reason, fashion girls (and pretty much everyone else) are entranced by her.

Recently noticing a plethora of available archival images of Wintour (dating back to the '80s), we did some digging to bring to you our favorite rare photos of the icon. The most fascinating result of our research was the distinct evolution of Wintour's style. While we familiarize her now with midi-length printed dresses and skirt suits, she once favored glamorous mini-length metallic shifts and Kate Moss–esque slip dresses. So basically, she was the most well-dressed woman in the '90s, too. Intrigued?

Keep scrolling to see 17 throwback Anna Wintour photos, starting in 1988.

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1988
(Image credit: Getty Images )

She's never been one to shy away from color. 

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1990
(Image credit: Getty Images )

She wears sequins well. 

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1991
(Image credit: Getty Images )

In case you were wondering, Anna wore a puffer to the ballet in 1991.

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1991
(Image credit: Getty Images )

Our next vintage store visit will be a scavenger hunt for a turtleneck like this.

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1991
(Image credit: Getty Images )

Yes, she once rocked the sheer trend, too.

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1993
(Image credit: Getty Images )

Yes, those are pink leggings you see. 

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1993
(Image credit: Getty Images )

Karl Lagerfeld, Anna, and Karl's fan.

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1995
(Image credit: Getty)

We'd gladly wear this exact dress today.

Related: All the Fashion Things Anna Wintour Hates (and Those She Loves)

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1996
(Image credit: Getty Images )

Just chillin' in the front row, as they do.

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1996
(Image credit: Getty Images )

Anna brought the chic '90s minimalism for an event with Princess Diana. 

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1999
(Image credit: Getty Images )

She wears her sunglasses at night. 

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2003
(Image credit: Getty Images )

What a trio!

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2005
(Image credit: Rex USA)

This photo of Anna and the late Bill Cunningham is perfection. 

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2006
(Image credit: Rex USA)

Behold tennis champ Roger Federer and his biggest fan, Anna Wintour.

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2009
(Image credit: Rex USA )

No Karl-and-Anna photo will ever beat this one. 

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2012
(Image credit: Rex USA )

If you're swooning over this coat, you're not alone. 

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2013
(Image credit: Rex USA )

Off she goes! 

Inspired by Wintour's affinity for metallics? Check out some of our favorite gleaming footwear.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.