Benjamin Ashford|See Olivia Wilde's Style Evolution Through the Years, From The O.C. to OMG

When did you first get a glimpse of Olivia Wilde?Benjamin Ashford

As bisexual "bad girl" Alex on The O.C.? As determined doctor Thirteen on House? Coming back to life in Cowboys & Aliens? Playing Justin Timberlake's mom in In Time? (It takes place in the future, don't ask.) Looking the picture of '50s-era domestic bliss in the unsettling drama Don't Worry Darling, which she also directed?

Point being, ever since she was first onscreen in the 2004 comedy The Girl Next Door, Wilde has been everywhere as an actress, filmmaker, activist and mom to daughter Daisy, 7, and son, Otis, 9, with ex Jason Sudeikis.

Her film debut was followed by her mid-aughts run on The O.C., during which she landed a lead role on the short-lived drama Skin and booked films like Alpha Dog and Turistas. And yes, they were hot girl roles, the lot of them.

She called directing the hit 2019 comedy Booksmart "the first job I've ever had that wasn't entirely dependent on and connected to my looks." But, she told the New York Times, she no longer felt pressured to play "everyone's version of a perfect woman."

And Wilde, who's turning 40 on March 10, used every opportunity she got as an actress to school herself in the craft of moviemaking.

"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: