The Rarest Anna Wintour Photos From the Past 30 Years

Allyson Payer

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 favourite rare photos of the icon. The most fascinating result of our research was the distinct evolution of Wintour's style. While we familiarise her now with midi-length printed dresses and skirt suits, she once favoured 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.

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

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