Olivia Wilde at Her Most Outspoken

Subscribe to Lucky

Deputy Editor

Halfway through a relaxed dinner at Venice’s Café Gratitude, Olivia Wilde is approached by an über-tan, McConaughey-esque stranger. After locking in on the actress, he saunters over and jumps into a pitch about an organic food documentary he directed, asking her (repeatedly) if she would be interested in helping him promote it.

She listens intently, cool-mint eyes fixed on the aging surfer dude as he goes on about genetically modified foods, chemicals, Prop 37 … She takes his card. She asks his name. She talks to him about the film. When he eventually leaves the table, he’s beaming.

Her ease throughout the whole encounter suggests that it isn’t the first time she’s gotten solicited like this. “It does happen a lot,” she admits. “But I feel I must be doing something right if people approach me with that kind of request. Earlier in my career, it was more women coming up and saying, ‘You’re my husband’s Hall Pass!’ *

*Hall Pass (n.) Slang term that refers to a celebrity a person would allow his or her significant other to freely hook up with without repercussions, due to the celebrity’s total amazingness.

“I was never sure what I was supposed to say to that,” she continues. “It was awkward. Back then, my public persona was vastly different from who I actually was. But over time people have started to understand what I’m about, and now when they come up to me they tend to do it without that sleaziness, which is nicer.”

After the success of indie romance Drinking Buddies and strong supporting roles in both Her and Rush, the world has definitely started to get a better sense of what Wilde is all about as an actress. And offscreen, the D.C. native has been making waves too. She and her fiancé, actor Jason Sudeikis, announced in late October that they were expecting a baby (a boy due, depending on when you pick up this issue, either in the past few weeks or any minute now), her charitable company, Conscious Commerce, launched its website in 2013 and she turned 30 in March.

In person, the actress is kind of everything you’d hope she’d be. Casually dressed in a soft, vintage MTV T-shirt from Junk Food that skims her slightly convex belly, American Eagle Outfitters jeans and Hudson boots (“good shit kickers”) with a well-worn Proenza Schouler PS1 bag, she carries herself with confidence. The Revlon spokeswoman’s otherworldly eyes are hard not to notice and her skin is perfect. A slightly stretched-out hair tie is the only thing adorning her wrist, which simply confirms that, as suspected, she’s one of us.

Wilde broke out in 2003 with a role in the short-lived drama Skin and then solidified her one-to-watch status with a turn as the controversial (read: Marissa Cooper–kissing) character Alex Kelly on The O.C. Since then, she’s acted steadily on TV (including a five-year run on House) while adding roles in Tron: Legacy, Cowboys & Aliens and In Time to her feature-film résumé.

“Your twenties are about hustling: getting into the workforce, making a name for yourself, supporting yourself, learning as much as possible,” she says of her early work. Now, she’s in fine-tuning mode. “It feels like this wonderful plateau, a vantage point where you can look and say, okay, now that I’ve seen all this stuff, I know which way I’d actually like to continue and what really isn’t true to me. That’s what’s happened over the last two or three years.”

Turning herself from a Hall Pass to, let’s be honest, a hybrid Hall Pass/activist magnet didn’t just happen overnight. Growing up, Wilde says, she was encouraged by her parents, journalists Andrew and Leslie Cockburn, to explore the world through first-­person experience—to always seek. “When I think of my childhood I imagine everyone reading: our long wooden dining room table, covered with every newspaper possible. And piles of books everywhere. My parents were always learning more. My mom picked up Arabic in her late forties.”

In 2009, the actress was one of the founding members of Artists for Peace and Justice, a group dedicated to raising money for medical care, education and food and water programs in Haiti, a country Wilde had visited with her family as a child.

She returned to Port-au-Prince in 2009 for the first time as an adult, and after the 2010 earthquake she went into what she describes as “maniacal fund-raising mode.” On one of her trips she met Barbara (“Babs”) Burchfield, co–executive producer of the Global Citizen Festival. The two hit it off and decided to start something new—Conscious Commerce, a company that had a charitable focus but also incorporated fashion, design and culture.

They began, in 2011, by looking at where money was already going. “We realized that people are already spending half a billion dollars a day in retail,” she says. “And that’s when the idea started germinating.” The duo felt there was value in encouraging people to shop from companies that were already doing something positive—be it by donating goods or money to those in need (like Toms or Warby Parker) or providing local employment (like Detroit watch company Shinola). In addition to putting these “conscious” companies in the spotlight, Wilde and Burchfield work to join brands with charitable organizations for limited-run product partnerships.

Conscious Commerce’s first collaboration, in 2012, was an Alternative Apparel messenger bag, inspired by the one Wilde wore when she visited Haiti in 2009. (Proceeds went to the Academy for Peace and Justice, a secondary school in Port-au-Prince.) The organization’s next project was a lace tea dress with designer Yoana Baraschi and Anthropologie whose proceeds went to the New Light girls’ school in Calcutta.

“We asked, ‘What’s a product that already sells well at Anthropologie?’ instead of trying to sell beaded wallets. It was about showing people that they can buy what they already want and have a positive impact.”

The mission is serious but the tone and expectation of Conscious Commerce is totally realistic—something that starts with the down-to-earth cofounders. “I wanted the language on the Conscious Commerce site (consciousco​.co) to be like you’re talking to your friends. It’s all about our attempt to live and exist and shop in a somewhat enlightened way. But without any sort of judgment.”

Wilde says she’s always wanted to get personally and physically involved with the work she’s doing. In an effort to learn more about the world, she wants to walk a mile in everyone’s shoes.

Well. Not everyone’s shoes, actually. “Eva Longoria always looks so put-together and goddamned adorable,” she says. “But I can’t imagine walking everywhere in those heels. She goes to the Laundromat with them on! I just don’t have it in me. My style is never uncomfortable … it’s part of my nature to look a little messy.”

Another way to say “a little messy” is tomboy-chic, a vibe that Wilde personifies by bringing elegance to a T-shirt and jeans and playfulness to a sleek Valentino gown. She cites Bob Marley and Keith Richards as early fashion icons and says she stole clothing out of her dad’s closet more than her older sister’s: “At 13 years old, I was wearing a lot of corduroy suits with wide-collared polyester shirts.”

The many vintage shops in D.C. allowed her to solidify her throwback style. “My nickname at that age was ‘thrifty girl,’ which I think of now and is so weird,” she says. “But at the time, I couldn’t imagine paying more than $20 for a pair of jeans.”

Now, her taste is a bit more refined. She favors brands like A.L.C., Rag & Bone, James Perse (“my new savior because of my expanding body”), J Brand, Rick Owens and Baldwin. She says she finds inspiration in other women, be it a perfectly put-together Eva Longoria or Blue Is the Warmest Color’s Adèle Exarchopoulos, whom she recently met at a panel discussion. “When in doubt, look to the French,” she concludes. “For literally everything in life. It’s just minimalism at its best.”

Street style is on her radar as well. After seeing girls in Paris wearing vintage tees tucked into pencil skirts a few years back, she says she thought she had solved the what-to-wear conundrum forever.

“I remember thinking, I’m going to go home and buy a bunch of pencil skirts so I can do that. The same thing happened with suspenders. I saw someone in suspenders and I thought, Yes! Suspenders are everything!”

Two things that don’t work very well at nine months pregnant, though, are suspenders and pencil skirts. So in recent months, Wilde has had to sail some uncharted sartorial seas.

Wanting to flaunt her shape was something that took her by surprise. “I just thought, Oh I’m going to hide this forever. But I ended up getting kind of excited to show the bump, as a badge of pride. Like,”—here she affects an Oprah-like bellow—“I’m a woman! Look at me making a human! I am a goddess!”

The bump wasn’t all—there’ve been other perks too: “I’m like, double D, hello! I’ve never been in this section of the bra store! I’ve been flat-chested my whole life, so it’s a wonderful new world.”

For all of the amazing, womanly changes pregnancy has brought there are also the weird, less-expected ones. For example, the switch that flips during your pregnancy and makes your skin ridiculously, unbelievably dry. “I’ve discovered some strong moisturizers throughout the process,” she says with a laugh. “The tube that’s in my purse and is with me at all times is Rodin cream. That stuff is dreamy.”

The rest of her current skincare routine, she divulges, is pretty simple. “I wash my face—revolutionary!—with a gentle cleanser like Kate Somerville Gentle Daily Wash and then use a good facial moisturizer. That’s it.”

As she leans in, Wilde has that definite radiance that pregnancy brings but, let’s face it, that skin was glowing always. What’s different, she says, is her new sense of calm. “Pregnancy does shed away all of the bullshit. It gives you more empathy because you look at everyone and you think, You were a baby!” It also, she says, has bonded her with other mothers. “Pregnancy brings you into this sort of commune—you feel connected to women in a way that you never have.”

As for her future baby boy, Wilde is enjoying her intimate relationship with him: “He’s moving around in there and no one else can tell—it’s a little secret friendship.”

She’s managed, thus far, to repel those who try to offer unsolicited advice. Specifically: those who want to see her and Sudeikis walk down the aisle (again—she was married from 2003 to 2011 to Italian photographer and filmmaker Tao Ru­spoli) before their son makes his entrance. “It’s certainly not something I feel pressured to do before we have the baby. I’m such a believer in marriage and I think of him as my husband anyway.” Their relationship sounds wonderfully, fabulously … normal. “I get that it’s not peaches and cream every day,” she says.

Her vintage engagement ring is perfectly suited for her, stunning and uncommon. A glint of green around a diamond shimmer. “All they know is that it went through Paris around 1921,” she says, twisting it around on her finger. “I love imagining the story of this ring. Who had it? It’s a bit of an aqua emerald, not a deep dark green. Jason said it reminded him of my eyes, which is very sweet.”

Wilde’s next role, playing opposite Liam Neeson in director Paul Haggis’ relationship drama Third Person (out in June), is that of a complex young woman who meets up with her lover, a writer, in Paris. “It was a totally different experience,” she says. “A really tough, tough part—the kind where you don’t have any fun after work, you just go home and face-plant.” Still, that’s the sort of character that appeals to her these days.

“Playing the ideal girl is much harder for me than the basket-case mess,” she says. “Now when I look at roles, if it says, ‘In walks in the femme fatale, the epitome of perfection and desire,’ I say, ‘No, that’s not going to work.’ I’m not interested unless she turns out to be psychotic and murders everyone in the room. I’d rather be Ursula than the Little Mermaid.”

In addition to producing two films later this year, she’s also returning to TV in an as-yet-unnamed HBO series alongside Bobby Cannavale, set within the NYC music scene of the late ’70s and produced by Martin Scorsese and Mick Jagger. (Let’s hope she kept a few of those Keith Richards–inspired corduroy suits in storage.)

First, though, comes the baby. After exploring far and wide, the biggest adventure that awaits Wilde ends up being such an intimately local one. She says she can’t wait to meet her “little person,” to see how he affects her evolution as work and love and travel have over the past decade.

“It’s funny to think about how long I’ve been in this business. It’s been 12 years yet people act like everything’s been an overnight success,” she says. “When I think about that, it makes me so curious about who I’ll be when I’m 70. We all thought we knew ourselves when we were 20 … We had no idea.”

WATCH: Behind The Scenes With Olivia Wilde At Her Lucky Cover Shoot

From our partners: