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.
She's never been one to shy away from color.
She wears sequins well.
In case you were wondering, Anna wore a puffer to the ballet in 1991.
Our next vintage store visit will be a scavenger hunt for a turtleneck like this.
Yes, she once rocked the sheer trend, too.
Yes, those are pink leggings you see.
Karl Lagerfeld, Anna, and Karl's fan.
We'd gladly wear this exact dress today.
Just chillin' in the front row, as they do.
Anna brought the chic '90s minimalism for an event with Princess Diana.
She wears her sunglasses at night.
What a trio!
This photo of Anna and the late Bill Cunningham is perfection.
Behold tennis champ Roger Federer and his biggest fan, Anna Wintour.
No Karl-and-Anna photo will ever beat this one.
If you're swooning over this coat, you're not alone.
Off she goes!
Inspired by Wintour's affinity for metallics? Check out some of our favorite gleaming footwear.