8 Reasons Why We Love Shailene Woodley's Style

In the grand tradition of YA leading ladies, Divergent star Shailene Woodley has perfected the art of heroine chic. But instead of bowing to trends, the outspoken, nature-loving actress chooses class over convention. That means she’s not afraid to flaunt trousers and a heel on a red carpet or eschew overt sexiness for a flowy printed dress—and the results are impressive. Here are some of our favorite looks and how you can steal Woodley’s confident style.

Jumpsuit and Bold Lip:


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For a New York screening of her new film, Divergent, Woodley opted for an Elie Saab Pre-Fall 13 Jumpsuit with sheer bodice detailing. She paired the jumpsuit with gold Rupert Sanderson pumps and a bright orange pout.


Takeaway tip: Minimal accessories and sleek hair add a youthful spin to a bold cocktail outfit.

Casual T-Shirt and Jeans


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At an after party for the New York screening of Divergent, Woodley changed into a pair of Citizens of Humanity Rocket High Rise Skinny Jeans ($188) and a camouflage t-shirt.


Takeaway tip: Style is confidence. Wear what makes you feel comfortable, and you’ll be totally Dauntless.

Crop Top and Flats:


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At the Independent Spirit Awards in Santa Monica, Woodley wore a crop top and floor length skirt by Lyn Devon (212.431.3777 for stores). Rather than teetering down the carpet in stilettos, Woodley opted to pair her outfit with Casadei Plaque Detail Flat Sandals ($568).


Takeaway tip: You don’t have to rock a heel to rule a red carpet. Pair a column skirt with flats for casual polish.

Pastel Shift Dress:


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At the 51st Annual Publicists Luncheon in Los Angeles, Woodley donned a chic jacquard shift dress from Jonathan Saunders’ Resort 2014 collection. The punchy neon color—which she echoes with her rose gold Gianvito Rossi Metallic Leather Sandals ($982)—keeps the traditional silhouette from feeling matronly.


Takeaway tip: Opt for bright hues when wearing classic pieces.  A pop of color can make even the most subdued silhouette stand out.

Sweater and Pants:


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For the Toronto premiere of Divergent, Woodley wore a nubby sweater, pinstriped shirt, and pailette-embellished pants from No. 21 and Kurt Geiger London Ellen Pumps ($300).


Takeaway tip: Menswear separates are cocktail appropriate when one item is in an evening fabric. Being bold is the true definition of heroine chic.

Cocktail Dress:


Monica Schipper/Getty Images)

At the 23rd Annual Gotham Independent Film Awards, Woodley eschewed jewelry and a bag in favor of sleek Calvin Klein Collection platforms, allowing this fringed halter dress from the brand’s S/S 14 collection to take center stage.


Takeaway tip: When the embellishment on your dress is the ultimate accessory, feel free to forgo jewelry and let your frock flag fly.

Crop Top & Mini Skirt:


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Woodley wore this outfit to the Video Music Awards in 2013. A mini skirt and crop top combination can quickly read cheesy, but the high neckline and sleek black pumps keep the look sophisticated.


Takeaway tip: Keep the extras sedate when exposing your midriff. Subdued and sexy aren’t mutually exclusive.



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Red carpet glamour doesn’t have to mean excessive displays of skin. Woodley’s Elie Saab Couture dress from the F/W 10 collection, which she wore to the Los Angeles premiere of Divergent, shows just hint of leg.


Takeaway tip: Choose a dress that draws attention to your favorite feature. The classiest women can shine in the most demure way possible.