17 Throwback Anna Wintour Photos You Haven't Seen

last updated 13 August 2019

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.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969540-1478642487 — 1988

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969554-1478642492 — 1990

She wears sequins well.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969541-1478642487 — 1991

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969542-1478642488 — 1991

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969543-1478642488 — 1991

Yes, she once rocked the sheer trend, too.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969545-1478642489 — 1993

Yes, those are pink leggings you see.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969549-1478642490 — 1993

Karl Lagerfeld, Anna, and Karl's fan.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969544-1478642488 — 1995

We'd gladly wear this exact dress today.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969546-1478642489 — 1996

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969547-1478642489 — 1996

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969550-1478642490 — 1999

She wears her sunglasses at night.

the-rarest-anna-wintour-photos-from-the-past-30-years-1969548-1478642489 — 2003

What a trio!

the-rarest-anna-wintour-photos-from-the-past-30-years-1969556-1478642494 — 2005

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969553-1478642492 — 2006

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969555-1478642492 — 2009

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969552-1478642491 — 2012

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

the-rarest-anna-wintour-photos-from-the-past-30-years-1969551-1478642490 — 2013

Off she goes!

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

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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.