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Olivia Wilde On Beauty Mistakes and the Makeup Look Men Are Afraid Of

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Courtesy Revlon

To look at Olivia Wilde now — she who looks flawless whether she’s walking the dog or at the Oscars — it’s hard to believe she ever had a bad beauty moment. But she swears she’s got one or two (or ten) in her past.

“I don’t think there’s one picture from growing up where I don’t think, ‘Ugh, awful!'” she tells PEOPLE. “If I ever have a daughter who starts experimenting with heavy makeup or shaving her hair like I did, I would encourage it and say, ‘Do it all now, you’ll learn yourself well.'”

Sorry: Shaving your hair? Are there photos of that? “I did that awful gutterpunk undershave look when I was 12,” she says. “Not an easy grow back process. It looked like I got run over by a tractor. But my mom had a good response to that stuff; I didn’t even need to be punished, I learned that one on my own.”

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These days, Wilde relies on a beauty routine much more low key than the ones you’ll see in her Revlon ads (the latest for the “Rio Rush” collection, seen exclusively at left, is a “sexy tan kind of Brazilian hot look”). Most days, she swipes on the brand’s CC cream to cover “any weird splotches and acne scars,” fills in her brows and puts on mascara.

For date night, she might add eyeshadow or contouring, but don’t expect to see her smooching fiancé Jason Sudeikis in super-bright lipstick. “I know that a glossy red lip is terrifying to a man,” she says. “It’s so funny because in every old movie they were clearly making out wearing heavy lipstick. How did they do it back then? Knowing the ’30s, they probably sprinkled lead on top to make it stay.”

Wilde may have come by her beauty lessons through trial and error through the years, but now she feels more confident in her look than ever. Even when a red carpet look goes wrong, “I never panic, I just say ‘Oh, I look like a drag queen, it’s not going to work,” she says. “I now know enough about my face to say, ‘Listen, that’s not going to work on me because of my man jaw or giant forehead.’ … [But] I encourage people to experiment, to have fun. When you feel your best, you look your best.”

What do you think about Wilde’s beauty mistakes? Do you have anything in your past that makes you cringe?

–Alex Apatoff