Shailene Woodley, Before and After

Shailene has been acting since age five, but she didn’t walk the red carpet until 16 (when she scored her first big leading role in The Secret Life of the American Teenager). I, for one, appreciate seeing that her teenage years were just as awkward as everybody else’s. Weird hair, zits, over-plucked brows... we’ve all been there. 

By age 17, her skin had cleared up and her natural medium brown hair had acquired a lighter, slightly reddish tint. But I’m not sure what’s going on with this updo (if you can even call it that, with the long pieces at the front). She’s also rocking an unfortunate style known as the “bang combover.”

While her previous look was kind of edgy, she next stepped out looking uncharacteristically sweet. The half-up waves (in a deeper brunette) and rosy flushed cheeks aren’t really her style, but even still, they’re very pretty. As for her features, we can see that her nose was definitely more prominent than most in Hollywood.

It wasn't until age 19 that she started to look more like the Shailene we know today. That’s also thanks to her styling team, of course—and she would’ve been working with the very best as a cast member of The Descendants. Although not long after this, she cut it all off, her hair at the time was glorious: long, thick and shiny, with the most beautiful sun-kissed Ombré.

You can always tell you need a haircut when you find yourself wearing a ponytail all the time. Maybe that’s what was happening with Shailene in 2012, when this was her go-to hairstyle (right before she got her dramatic, career-changing chop). I especially love her bold red lipstick and defined lashes.

Then, she lopped off her hair—and like so many actresses before her, this pixie cut surely helped propel her to new levels of stardom. (It’s practically a rite of passage for young celebs, but in this case, I think it really suits her!) Sometimes, celebs use a radical haircut to distract us from a sneaky cosmetic procedure or two, but I don’t see any evidence of that here.

I don’t know about you, but when most celebrities get short hair, I can’t wait for it to grow back. (See: Katy Perry and Scarlett Johansson, for starters.) Not so with Shailene. She looks incredible in this pixie, even with barely any makeup. With the slicked-down style, blonde highlights and a subtle tan, I’m into this whole vibe.

Nobody said that growing out short hair would be easy. While I can appreciate her solution of a reverse French braid, Shailene is definitely going through that awkward in-between phase. It doesn’t help that the makeup is washing her out, which might be because she only lets organic products touch her skin. We all know how hit-and-miss organic foundations can be (or at least they were, back in 2015!). 

A year later, Shailene debuted another radical beauty transformation: a deep tan, much longer hair (thanks to extensions), and a dark brunette colour. I’m not a fan of the latter, which doesn’t have enough dimension. But I do like the rest, including the nose ring. Speaking of noses, I don’t see any change there so far.

The hair changes keep on coming, and this might be the most unexpected look yet. Much to everyone’s surprise, she showed up to this red carpet as a bleached blonde. (Actually, there are a few different tones going on here—cool blonde, brassy blonde and visible roots—but they somehow look a lot better on her hairstylist’s Instagram.) For someone so into natural living, it just seems off-brand. 

She kept the blonde through 2018 (she was 26 by this point), but with a few inches of regrowth and a more gradual transition, it looked a lot more realistic. Her makeup game improved, too. Her eyes are enhanced with just the right amount of smoky shadow, and the red lipstick adds a face-brightening pop.

Shailene’s personal style got even bolder the following year, when she wore this dramatic hat (complete with matching suit) to an A-list party. After all these years on the red carpet, she’s now got the necessary confidence to pull it off. You might’ve noticed that her lips seem fuller than usual, but if you zoom in, it’s just because they’ve been lined outside the edges.

And that brings us to her most recent red carpet appearance, where she went all sultry and sleek in smoky eyes and straight, half-back hair. It’s her skin finish that keeps this from being too “done”—if she wore a full face of foundation, she wouldn’t look like herself at all.

With her hippie reputation, Shailene is the last person you’d think would undergo cosmetic enhancements, despite being among the highest-paid working actresses today.

As far as I can tell, any changes to her facial features appear to be a result of clever makeup techniques and normal aging—not plastic surgery.

She has even rallied against Photoshopped images of herself being used in the media. “The reality is that I do not have those lips and my skin is not flawless and I do have a little bit of a stomach. It was not a proper representation of who I am,” she told Interview.^[3]

She even tries to keep it real when getting glammed. “Day-to-day, I don’t wear makeup at all. I will get my makeup done for appearances and events. You have to pick and choose where you are going to represent you and the things you keep sacred, and then there are the things you have to do for the public.... I respect the establishment, but I don’t sacrifice my own integrity. I wouldn’t wear fake eyelashes or crazy extensions. It’s always me—just maybe the public, pretty-in-a-Cinderella-dress me,” she explained to Into The Gloss.^[1]

After all, she has a bigger goal in mind than just personal fame. “[Celebrities] can make this about ourselves given the platform that we have, or we can use it for a cause,” she said in an interview with Global News. “Use all this attention for something that’s greater than just an individual life.”^[4] As an avid environmental and political activist, she is doing just that!