“Despite how externally positive I might have been, I was internally at war with myself throughout a lot of my 20s.”
Shailene Woodley and I are on a cross-country phone call talking about our impending “Saturn returns.” As common a Southern California expression as “June gloom” or “pilot season,” Saturn return describes an astrological event that takes place when Saturn moves back to the position in space where it was when a person was born—approximately 29.5 years later. “I’m not one for dogma or doctrine of any kind,” Woodley qualifies when I ask her how closely she adheres to astrology or spiritual ideology of any kind. “But I deeply believe that if things have been around for thousands of years, then there must be some wisdom in there.” Woodley and I, both 27, seem to agree that while the planets may not be directly impacting our destinies, there is an undeniable change that occurs in one’s late 20s. At this age, we seem to move past all the aimless tumult we experienced at the beginning of adulthood—a time of professional unpredictability, financial instability, and the awkwardness of still not having your look quite figured out. Woodley describes 27 as the start of her pilgrimage back to a more relaxed, almost childlike state. “I feel a resurrection of the freedom that I experienced when I was about 17—this beautiful 10-year cycle,” she continues. “Despite the raging hormones and not-so-great boyfriend I had at the time, I still had a sense of wonder. I feel like I allowed that wonder to be crushed. But it’s being brought up from the ashes at the moment.”
Rebekah Campbell; STYLING: Rentrayage coat; Jordache Rinse Diagonal Logo Print High-Rise Shorts ($195); PH5 Ivy Logo Embroidered Rib Polo Shirt ($215); De Cosmi Maxima Earrings ($2475); Rombaut Socks ($28) in Acid
Today, Woodley is best recognized for her role on the hit HBO series Big Little Lies, in which she stars alongside Hollywood powerhouses like Nicole Kidman, Reese Witherspoon, and, as of season two (premiering June 9), Meryl Streep. The Simi Valley, California native first rose to fame in 2008 as the 16-year-old protagonist of the ABC Family TV drama The Secret Life of the American Teenager. Lead roles in big-screen blockbusters like 2011’s The Descendants, starring George Clooney; the sci-fi action Divergent trilogy; and The Fault in Our Stars positioned Woodley, with her openhearted quality of performance and charm, as one of the most prominent ingenues in mainstream entertainment. But offscreen, Woodley was cultivating a quirkier reputation. Throughout her early 20s, the actress flummoxed reporters and talk show hosts with her bohemian, profoundly un-Hollywood approach to beauty and lifestyle. Flower child–ish, Goop-esque practices like oil pulling, DIY'ing toothpaste from clay, and using spirulina as eye shadow were among the Woodley-isms that made the news. “Are Shailene Woodley’s Natural Beauty Hacks Safe?” a 2017 StyleCaster headline read. “‘Divergent’ Star Shailene Woodley Is a Queerish Hippie Who Believes in Trees,” read an Autostraddle title from a few years earlier.
It was challenging for Woodley to experiment with her ideologies and aesthetic (in the way that all 20-somethings do) knowing that a snarky headline might result. In her public appearances throughout the mid-2010s, she was always bubbly and smiling, but Woodley wasn’t immune to the criticism—from the press, certainly, but mostly from within. “I’m an optimist by nature,” she says. “But in my 20s, a lot of my internal speak became more aggressive and negative. I knew I could always make someone else’s day better, but I didn’t know how to make my internal world better.”
What didn’t help Woodley along her path to self-discovery was the pressure from stylists to temper her look on red carpets. “When I became really successful in the public eye, my identity felt compromised,” she explains, “because I was thrown into a situation where I would show up to a room, and there would be 13 dresses, and I had to pick one of them. They were beautiful, but I never felt like any of them represented my style.” Woodley would try suggesting they add a funky hat or some interesting jewelry but largely felt ignored, so she stopped trying. “I am the queen of saying no,” she swears. “But for some reason, with fashion, it took me a long time to be able to stand up for myself, to express myself and my personal identity, in the way I do in every other facet of my life.” Woodley recalls one red carpet event when she was practically forced into a couture gown. “I felt like a mannequin, like a fairy princess,” she describes. “I got on all the best dressed lists, but it felt gross to me.”
Over the past couple of years, improving her internal narrative has been Woodley’s main mental health focus. Her career, relationships, and style are all the better for it. Woodley credits talk therapy, spending time in nature, and reading religious and spiritual scriptures (“I find myself becoming more attracted to people of faith,” she says) to her serener homeostasis. “I am finding that my internal world and my external world are slowly morphing into one, which is really reassuring,” she says with relief. “It doesn’t mean that it comes without obstacles, trial, or tribulation, but it does allow for a more peaceful existence and kinder self-talk.”
Woodley says her fellow Big Little Lies cast members have also had a profoundly positive impact on her life and career. When asked to name a piece of wisdom she’s gleaned from each woman—Nicole Kidman, Reese Witherspoon, Laura Dern, Zoë Kravitz, and Meryl Streep—she answers:
“With Nicole, I feel like I could stare into her eyes for hours and leave all the wiser and more grounded simply because of the energy she holds. Reese is one person who I know, despite what may be thrown at her, is going to forge through and powerfully fight for cataclysmic change with a certain grace—even if it’s not initially interpreted as grace. Laura is someone who knows how to make every single person around her feel as if they’re the most important person in the room, as if they’re someone who deeply matters. Meryl has an infinite supply of passion and humility, and that’s wisdom I gained just from watching her. (I’ve often found in this industry that people at the top, the ones who are the most successful, are also the humblest, the kindest, and most generous.) Zoë: I grew up next to her. We have done five projects together now between the Divergent series and Big Little Lies. We have gone through most bumps that any normal friendship goes through when you’re in your 20s, but we’ve still been able to find love for one another. And I think that there is a wisdom in that.”
Woodley categorizes where she is now, mentally and aesthetically, as “a completely different space.” Her past two years of red carpet looks serve as evidence, albeit surface-level, that the actress has truly come into her own. After ditching her old stylists and putting herself through a minimalist wardrobe detox, in which all the clothes she owned personally could fit into a small suitcase, Woodley decided to revisit the world of fashion. “My relationship with clothes has changed so much,” she gasps. Recently, Woodley began attending fashion weeks and familiarizing herself with designers. She came to appreciate couture as a form of artistry instead of the identity-crushing behemoth it once was. “I became blown away by designers’ process and completely moved by the art,” she says. Woodley began working with stylist Micaela Erlanger, who she says totally grasps the playful, eccentric public image she’s trying to create. (Check out the red-feather Attico number she dressed her in for the Scarlet Night party earlier this year, or the sunny yellow embellished trench she wore to Carolina Herrera’s show at NYFW.)
Underneath Woodley’s chic exterior, however, the offbeat hippie remains. In fact, approximately eight minutes of our phone conversation are spent discussing her favorite tree (a massive oak in her hometown). Woodley wears the tree-hugger label with pride. “I don’t hug a tree for no reason,” she says. “There’s an extreme exchange of energy and wisdom that happens when you spend time in nature, and it’s not something to make fun of. It’s something to revere.”
Even as her Big Little Lies fame continues to explode and her Saturn return locks into its cosmic place, Woodley maintains that her journey to self-realization soldiers on. She’s still in an ongoing process of negotiating her identity; she’s simply a little nicer to herself than she once was along the way.
“It’s a curious time for me,” Woodley tells me wistfully. “But a beautiful one.”