Shailene Woodley first gained notoriety for her role in the ABC Family series The Secret Life of the American Teenager, but the young beauty is on her way to superstar status with starring turns in The Descendants, Divergent, and The Fault in Our Stars, opening today, already under her belt. Shailene has handled her newfound spotlight like a pro and isn't afraid to take a risk or buck the trend. You may recall InStyle's 2012 Golden Globes afterparty when Shailene traded her high heels for a pair of Vibram FiveFingers running shoes, a bold move for any starlet new to the fashion world's hypercritical lens. Don't get us wrong, the cover girl has scored high remarks on her red carpet report card, but we're particularly smitten with her instinctive confidence.
With nothing but Hollywood hits and designer duds in her future, we're honoring the release of Shailene's latest blockbuster with a fashion flashback of her classic yet bold, laid-back glamour.
— Additional reporting by Brittney Stephens