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
Shailene Woodley in Ralph Lauren Collection at The Fault in Our Stars 2014 NYC Premiere
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.
Shailene Woodley in White Zuhair Murad Gown at the 2014 Divergent Berlin Premiere
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.
Shailene Woodley in Roksanda Ilincic at the 2014 Divergent Mexico City Premiere
Her tangerine Roksanda Ilincic column gown brightened up the red carpet in March 2014.
Shailene Woodley in Leather Balmain Duo at the 2014 MTV Movie Awards
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.
Shailene Woodley in an LBD at the 2014 Hollywood Film Awards Gala
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.
Shailene Woodley in Donna Karan Atelier at the 2014 Divergent Madrid Premiere
Va-va-voom! Shailene swapped her youthful exuberance for a sultrier vibe in Donna Karan Atelier in April 2014.
Shailene Woodley in Stella McCartney at the 2014 Divergent European Premiere
Woodley was bringing sexy back in a cutout lace-trim Stella McCartney for the European premiere of Divergent.
Shailene Woodley in Jason Wu at the 2012 BAFTA Los Angeles Awards Tea Party
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.
Shailene Woodley in Floral Dolce & Gabbana at the 2011 Descendants LA Premiere
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.
Shailene Woodley in Prabal Gurung at a 2011 Hollywood Reporter Breakfast
For a Hollywood Reporter event, Shailene mixed things up in a chic, youthful Prabal Gurung combo dress and Rachel Zoe  Collection pumps.
Shailene Woodley in an Elie Saab Jumpsuit at the 2014 Divergent NYC Screening
For a 2014 Divergent screening, Shailene proved the power of the jumpsuit in Elie Saab.
Shailene Woodley in Marchesa at the 2012 Golden Globes
For the 2012 Golden Globes, Shailene pulled out all the stops in this breathtaking, soft lilac-colored Marchesa gown.
Shailene Woodley in L'Wren Scott at a 2011 NYC Event
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 Woodley in Christopher Kane at the 2012 LA Film Critics Association Awards
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 Woodley in Calvin Klein at the 2012 Critics' Choice Movie Awards
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 Woodley in a Dolce & Gabbana Suit at the 2011 Gotham Independent Film Awards
Shailene's spin on menswear: a Dolce & Gabbana suit with gray suede pumps and a long, sideswept fishtail braid.
Shailene Woodley in a Lace Honor Mini at the 2011 AFI Awards
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.
Shailene Woodley in Rodarte at the 2014 Met Gala
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.
Shailene Woodley in Valentino at the 2012 Producers Guild Awards
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.
Shailene Woodley in Lace Valentino at the 2012 Directors Guild of America Awards
For the 2012 Directors Guild of America Awards, Shailene oozed sophistication in a rich sheer lace Valentino stunner.
Shailene Woodley in Floral Appliqué L'Wren Scott at the 2012 Screen Actors Guild Awards
Shimmering in a sleek floral L'Wren Scott gown with blue-and-red flower appliqué gown in January 2012.
Shailene Woodley in Leather 3.1 Phillip Lim Mini at the 2012 Santa Barbara International Film Festival
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 in Tulle Gown at the 2012 Orange British Academy Film Awards
Shailene Woodley chose a strapless tulle gown and ballerina bun for the Orange British Academy Film Awards in February 2012.
Shailene Woodley in Christopher Kane Top at the 2012 Independent Spirit Awards
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.
Shailene Woodley in White Valentino Gown at the 2012 Oscars
Graduating to grecian goddess status in a s-t-u-n-n-i-n-g Valentino gown for the 2012 Oscars.
Shailene Woodley in Proenza Schouler at the 2012 Vanity Fair Oscars Party
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.
Shailene Woodley in a Floral Honor Maxi at The Hunger Games 2012 LA Premiere
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 Woodley in Floral Christopher Kane Gown at the 2012 Met Gala
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.
Shailene Woodley in Calvin Klein at the 2012 Cannes Film Festival
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 Woodley in Stella McCartney at the 2012 MTV Movie Awards
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.
Shailene Woodley in Proenza Schouler at a Spectacular Now 2013 LA Screening
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.
Shailene Woodley in Jonathan Saunders at a 2014 Luncheon
For a February 2014 luncheon, Shailene looked Spring-fresh in a subtly embossed Jonathan Saunders sherbet sheath.
Shailene Woodley in Colorblock Calvin Klein at the 2013 Elle Women in Hollywood Event
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 Woodley in Alexander McQueen at the 2014 Divergent Atlanta Screening
Shailene amped up her embossed white sheath with statement sandals, both by Alexander McQueen.