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
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For The Fault in Our Stars NYC premiere, the leading lady posed in a brilliant Ralph Lauren Collection column gown featuring a figure-flaunting peplum bodice and sleek skirt.
Woodley oozed sex appeal at Divergent's 2014 Berlin premiere in a plunging Zuhair Murad Pre-Fall 2014 gown. Her best accessory? The devastatingly handsome Theo James.
Her tangerine Roksanda Ilincic column gown brightened up the red carpet in March 2014.
It was all about edge for Woodley's 2014 MTV Movie Awards ensemble. From the rugged olive-hued leather to the the sexy twist-front detail, we loved everything about her Balmain duo.
For the Hollywood Film Festival, Shailene wore a simple yet chic black tank dress with black pumps, and showed her altruistic side with a Judith Leiber Feed 1000 clutch.
Va-va-voom! Shailene swapped her youthful exuberance for a sultrier vibe in Donna Karan Atelier in April 2014.
Woodley was bringing sexy back in a cutout lace-trim Stella McCartney for the European premiere of Divergent.
The young actress wore a Jason Wu tea-length dress in an abstract, geometric print — proving she isn't afraid to shake things up with a pattern from time to time.
For the 2011 red carpet premiere of The Descendants, Shailene chose an ultrafeminine black floral tea dress by Dolce & Gabbana. Her full-skirt frock was teamed with Rachel Zoe Collection pumps.
For a Hollywood Reporter event, Shailene mixed things up in a chic, youthful Prabal Gurung combo dress and Rachel Zoe Collection pumps.
For a 2014 Divergent screening, Shailene proved the power of the jumpsuit in Elie Saab.
For the 2012 Golden Globes, Shailene pulled out all the stops in this breathtaking, soft lilac-colored Marchesa gown.
Woodley attended an event in November 2011 in a bordeaux-colored L'Wren Scott dress that featured black beaded embroidery. It was a mature look that proved that the actress can fit in perfectly with fashion's older, more experienced heavy hitters.
Shailene wore an iridescent Christopher Kane dress in a pretty, abstract floral print with a sexy open back. She paired the mini with a beautiful pair of bright blue Ferragamo sandals for the perfect pop of color.
Shailene stunned at the 2012 Critics' Choice Movie Awards, choosing a gorgeous gray Calvin Klein gown with an open back and metallic silver neckline.
Shailene's spin on menswear: a Dolce & Gabbana suit with gray suede pumps and a long, sideswept fishtail braid.
For the AFI Awards in early January, the actress opted for a creamy lace minidress from Honor's Spring '12 collection. We love how dainty and sweet the dress is, especially with Shailene's long, sexy legs.
The star wowed at the 2014 Met Gala in an opulent Rodarte Fall 2014 creation that highlighted her sculpted shoulders and gave a peek at her toned stems via sheer lace overlay.
Black velvet in that little girl's (vibrant) smile. The actress went back to basics in a supple Valentino minidress, sparkling sandals, and a punchy red lipstick in 2012.
For the 2012 Directors Guild of America Awards, Shailene oozed sophistication in a rich sheer lace Valentino stunner.
Shimmering in a sleek floral L'Wren Scott gown with blue-and-red flower appliqué gown in January 2012.
Woodley edged up her usually sweet style with a navy leather 3.1 Phillip Lim mini and strappy suede heels for the Santa Barbara International Film Festival.
Shailene Woodley chose a strapless tulle gown and ballerina bun for the Orange British Academy Film Awards in February 2012.
The "Best Supporting Female" winner nailed casual chic, topping her black denim with an ornate gold-and-pink Christopher Kane top and cap-toe Christian Louboutins at the 2012 Independent Spirit Awards.
Graduating to grecian goddess status in a s-t-u-n-n-i-n-g Valentino gown for the 2012 Oscars.
A Proenza Schouler floral embroidered dress epitomized the young actresses's fresh and fuss-free style for Vanity Fair's 2012 Oscar party. The Hollywood darling completed her Spring-ready style with lime green Diane von Furstenberg pumps.
For The Hunger Games LA premiere, Shailene looked Cali-cool in a silky floral Honor maxi detailed with low-key pockets and a sexy deep neckline.
Shailene showcased her penchant for effortless glamour owning a slick Christopher Kane floral-infused column dress, featuring edgy leather detailing and high-low sheer proportions, in 2012.
Talk about an orange crush. Woodley chose a sleeveless salmon Calvin Klein dress for a 2012 Cannes Film Festival party thrown by the design house.
Shailene showed off her enviable curves — who knew she was hiding those bad boys?! — in a low-cut halter vest, featuring a sweet peplum-esque trim, slick black trousers, and dainty ankle-strap sandals, all by Stella McCartney, at the 2012 MTV Movie Awards.
Nailing the perfect balance of style and comfort in a cropped turtleneck and draping calf-length skirt, both by Proenza Schouler, for The Spectacular Now premiere in July 2013.
For a February 2014 luncheon, Shailene looked Spring-fresh in a subtly embossed Jonathan Saunders sherbet sheath.
The star celebrated ELLE's 20th's Women in Hollywood celebration in a paneled printed Calvin Klein creation complete with skin-baring side cutouts.
Shailene amped up her embossed white sheath with statement sandals, both by Alexander McQueen.