See Olivia Wilde’s Style Evolution Through the Years

“I’m still learning so much every day,” she told People at the 2020 Sundance Film Festival. “It feels like a pivot, but one that is healthy and allows you to appreciate every experience you’ve had.”

And while telling useful stories is her primary goal, take one look at the jaw-dropping production design of the much-buzzed-about Don’t Worry Darling or her history of glamorous red carpet looks, and it’s clear the artist—who had no qualms about freeing the nipple during Paris Fashion Week last month—is also seriously committed to style.

Not that she had all the answers right out of the gate.

“I dressed like Johnny Lee Hooker had a baby with John Belushi,” she told W in 2023, describing her fashion aesthetic as a teenager. “But I think I was going for a Françoise Hardy thing in my head? Lots of corduroy bell bottom suits. Probably too many sweatshirts. Vintage jeans were a real passion of mine. I felt like I had a gift of identifying great denim. When I look back at photos now, I’m not so sure. But I was an individual, which I’m proud of. Always a weirdo.”

And always a stunner. Keep reading to see Wilde’s style evolution over the course of her long, ever-evolving career:

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