The Fashion Evolution of Shailene Woodley: From Hippie Chic to Full-On Sleek
1/27The Divergent Series: Alligent is finally here, giving followers of the film the next chapter of Tris and Four’s story. But the arrival of the film isn’t just for Divergent-lovers — all the premieres and appearances give fashion fans even more outfits from star Shailene Woodley to covet and copy.
Shailene has become an icon for her sleek jumpsuits and flawless gowns, but this look is a far cry from the cropped pants and printed tees she wore when she first came onto the scene. Shailene got her start as a child model before landing major roles in The Secret Life of the American Teenager, The Fault in Our Stars, and, yep, The Divergent Series, so she knows a thing or two about the world of style.
Click through to see the star transition from printed separates and matchy-matchy ensembles to the Oscar-worthy gowns she’s known for today — you’ve never seen a transformation quite like this.
Photo: Frazer Harrison/Getty Images2/27April 2006
Shailene, is that you?! The star looked unrecognizable — but oh-so-cute! — in this fun multi-colored tee, cropped pants, and metallic shoes look for an American Girl Store Opening. We wonder which doll she picked out…
Photo: Steve Granitz/WireImage3/27August 2008
By 2008, Shailene was starring on The Secret Life of the American Teenager (R.I.P.), and took to the annual Teen Choice Awards to show off her new boho-chic style. Her dress may have been perfectly simple, but gold flat sandals and tons of extra-long beads added the right touches fitting the L.A. event.
Photo: Steve Granitz/WireImage4/27November 2008
Shailene rarely steps out in super high heels, so this outfit (for the 2008 American Music Awards) was especially noteworthy. Perfectly matching her high-necked dress, this all-grey look was actual #promgoals.
Photo: Steve Granitz/WireImage5/27August 2009
Her style may lean towards the minimal these days, but Shailene had her funky days. This printed blouse, paired with high-waisted shorts and black high-heel sandals, was one of her most memorable to date.
Photo: Jon Kopaloff/FilmMagic6/27September 2009
Shailene stole the show at Teen Vogue’s annual Young Hollywood Party in this emerald green dress. Sometimes less is totally more.
Photo: Jason Merritt/Getty Images7/27August 2010
The star put her own spin on the classic LBD for the 2010 Teen Choice Awards with thick ankle-strap sandals and an easy updo. Make it a flat and this is your go-to outfit for a dressy movie night with friends.
Photo: Michael Kovac/Getty Images for EGPAF8/27June 2011
Shailene will always have a soft spot for boho style — as you can see by this layered look from an L.A. charity event. She may be mixing tons of textures, but her minimal makeup and sleek blown-out hair keep things looking totally pulled together.
Photo: Jon Kopaloff/FilmMagic9/27November 2011
Shailene got her big screen break in 2011’s The Descendants — and celebrated in appropriately formal fashion. Her messy French-inspired bun, her strapless floral frock, and her sleek black pumps? Perfection from head to toe.
Photo: Michael Loccisano/WireImage for IFP10/27November 2011
Is there anything chicer than a classic black suit? (No.) Shailene took hers to the next level with a cool, undone fishtail braid and sleek grey pumps. Add this to your “looks to try” Pinterest board stat!
Photo: Jon Kopaloff/FilmMagic11/27January 2012
Shailene debuted her best look yet at the 2012 Critics Choice Movie Awards. Easy straight hair, a perfectly fitted grey dress, and minimal accessories? Yes, please!
Photo: Pascal Le Segretain/Getty Images12/27February 2012
Shailene looked super fresh at a 2012 Oscar party in this long-sleeved shift. Her suede shoes matched perfectly, while her simple updo keep things more modern than matchy.
Photo: Tommaso Boddi/Getty Images13/27February 2012
Now this is how you wear a leather minidress! Shailene’s shift has a loose fit, which is comfy and chic. Her simple hair and makeup and lace-up nude sandals are all she needs to finish the look.
Photo: Dan MacMedan/WireImage14/27February 2012
Her film The Descendants was nominated for an Academy Award (major!), so Shailene hit dressed up to show her support. Long-sleeved and elegantly simple, this ivory Valentino couture gown was the perfect choice.
Photo: Alberto E. Rodriguez/Getty Images15/27August 2013
Ooh la la! Consider Shailene’s crop top and embellished skirt look for your next date night. Bonus points for dark liner and gelled-back hair like hers!
Photo: EMMANUEL DUNAND/AFP/Getty Images16/27February 2014
Shailene showed off the perfect daytime formal dress at an event in 2014 with simple sandals and side-parted hair. Graduation is right around the corner, you know…
Photo: Jason LaVeris/FilmMagic17/27March 2014
Shailene loves a good two-piece. By matching the top and skirt (and adding a minimal gold pendant necklace), she makes it appropriate for a major event.
Photo: Getty Images for CinemaCon18/27March 2014
Just when we thought it couldn’t get any better, Shailene donned this black satin suit. Ruby red pumps and a chic ankle bracelet were just icing on the cake.
Photo: Jason LaVeris/FilmMagic19/27April 2014
Shailene killed it in this leather Balmain top and skirt at the MTV Movie Awards. From her brushed-over hair to her woven black sandals, this look was a win from head to toe.
Photo: Axelle/Bauer-Griffin/FilmMagic20/27May 2014
It’s not easy to stand out at the beyond-glamorous Met Gala, but Shailene managed to do just that in this multi-printed Rodarte dress.
Photo: Stephen Lovekin/Getty Images21/27June 2014
Has a bright yellow gown ever looked this good? Shailene proves an impeccable fit can make anything work in this bright dress.
Photo: Jason Merritt/Getty Images22/27November 2014
Shailene doesn’t often go for the princess gown, but when she does, she always nails it. By keeping her hair and makeup minimal and rarely piling on the jewels, the star looks natural and at ease in everything she wears.
Photo: Jim Spellman/WireImage23/27March 2015
Shailene? More like Slaylene! This slit-leg black gown was one of the star’s best looks ever.
Photo: Karwai Tang/WireImage24/27March 2015
Another day, another gorgeous white dress. Shailene was already the center of attention at the Insurgent World Premiere, but this short-sleeved white gown helped her truly steal the show.
Photo: NBCU Photo Bank via Getty Images25/27March 2016
How cool is this skyline dress? Her strappy silver sandals and new dark ‘do made the look pop even more.
Photo: Mark Sagliocco/Getty Images26/27March 2016
March 2016 Shailene’s worn plenty of jumpsuits in her lifetime, but none as glamorous as this. Fully embellished and paired with elegant pointy pumps, the actress proved her days of boho sweaters and printed tees are firmly in the past.
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