15-Year-Old Pop Star Grace VanderWaal Is Becoming a Style Icon Before Our Eyes

When Grace VanderWaal, winner of America’s Got Talent 2016, made her first television appearance, she was wearing a white button-down with a Peter Pan collar tucked under a navy blue sweater with skinny jeans the color of a daffodil. A meticulously flat-ironed bob and straight-across bangs framed the then 12-year-old’s earnest face as she dumbfounded the audience with her belting, raspy voice and songwriting genius. Rolling Stone quickly labeled her a "pop prodigy.” Simon Cowell christened her "the next Taylor Swift.”

Fast-forward three years, two studio albums, a Billboard Women in Music Rising Star award, a lead acting role in Disney’s newest film Stargirl (set for 2020 release), and a one-of-a-kind haircut—an ear-length crop featuring two shoulder-length pieces on either side of her face. Now VanderWaal is looking less like the prim tween we first met and closer to a grown-up artist with an edgy perspective. Think less Taylor Swift, more Sia. Though, luckily, her sense of childlike whimsy hasn’t budged. "I just had this vision of having two super-long braids in the front, like down to my knees, and everything else super short,” VanderWaal tells me over the phone, describing the inspiration behind her devastatingly cool, undeniably weird new look. "I have yet to fulfill that dream, but that was the initial vision when I cut my hair.”

During adolescence, time works differently. Weeks unfold like months, and as you’re developing your identity, change and experimentation seem to happen at a breakneck pace. Clothes, whether or not you’re walking red carpets and doing photo shoots, play a huge role in that investigation. VanderWaal smiles through the phone as she tells me about a voluminous, ruffled lime-green Marc Jacobs S/S 19 dress she wore to the premiere of Wonder Park (an animated adventure movie that came out in March, for which she recorded her first soundtrack song, "Hideaway”). "That was the funnest thing I’ve ever done,” she gushes.

We caught VanderWaal in Los Angeles to play dress-up, snap some photos, and ask her a few style questions. Keep scrolling to read about the music wunderkind’s fashion icons, her favorite places to vintage-shop, and why her ultimate style goal is to "look like an alien.”

How would you say your style has changed since you won America’s Got Talent?

I’ve always sort of known what I like and what I want to wear. Honestly, the best way my style has evolved since then has to do with the people around me getting to know that and letting me have more freedom. I also love that I’m getting older because all my life, I’ve always loved high fashion and editorial stuff, but it used to be kind of weird for me to wear it. So I’m really happy that I get to experiment with that a little bit now. I just recently wore Marc Jacobs to a red carpet, and I loved that.

Your fashion vibe has such a strong perspective. How do you decide what to wear?

I’m really drawn to funky stuff. The whole alien-esque aesthetic is beautiful. I just want to look like an alien. Always alien vibes with me. But I pretty much go for whatever I feel fire in. It doesn’t even matter what it looks like; it matters how I feel in it. If my clothes change the way I walk, then I know I am in something perfect.

What does a fire walk look like?

A fire walk is when you put on clothes and can’t seem to move like you normally would. For some reason, you can only strut. You can only take big strides because you feel that good.

Who are your ultimate style icons?

Audrey Hepburn. And Lily-Rose Depp has some killer style.

Where do you like to shop for everyday clothes?

Thrift shops. Princess Polly is a great online store. And every time I’m in L.A., I go to American Vintage. That is the most fire store. I can always find really cool stuff there.

What is your favorite vintage piece you own?

I have these bell-bottom overalls. They are so great. I love them so much. I wear them as pants and as overalls all the time. I don’t think I could live without them. They were my dad’s when he was younger. I honestly get my best vintage clothes from my parents, especially my dad because he has a lot of ’70s clothes since he’s older.

So lucky that he kept them! What’s your favorite red carpet look you’ve worn so far?

Probably that Marc Jacobs dress. That was the funnest thing I’ve ever done. Also for the Billboard Women in Music Awards this year, I wore this green outfit and felt so beautiful. Super good and comfortable.

Has there ever been a time when you felt pressure to wear something you didn’t feel super yourself in?

Oh yeah. I wear things that I’m not super crazy about all the time. Just because sometimes there aren’t enough options, and I don’t like anything else, and it’s a time crunch. I feel bad saying that because I don’t want people to look at it differently. But you can’t feel like yourself every single day. I’m a very "what are you gonna do?” type of person, though. If there’s nothing else I can do, might as well just try to feel myself.

What’s the outfit you feel the most yourself in?

That’s such a hard question because I’m so different every single day. Some days I like to dress like a rocker-chick bum, and other days I like to dress like a super-preppy boss lady. It all depends on my mood because I feel so good in both of those opposite styles.

What does your boss-lady outfit look like?

It will always be a young men’s button-up and an oversize blazer with my hair slicked back and some earrings. That is always a win for me when I want to look like a boss. I always feel so good in that outfit.

What are your current makeup favorites?

I would not look the way that I do in my day-to-day life if it weren’t for my job because I pick up so many products and techniques. I love hydrated, glowy skin. Milk and Glossier are my two favorite brands. Milk has great mascara and brow gel. I love its cream products, like its blush. And I use Glossier’s lipsticks the most. Its face gloss—all its glossy products are amazing.

Who are your beauty icons?

@Uglyworldwide. Always. She is genuinely fire to me. Seriously, she is stunning to me. Every single time I’m on a red carpet, my makeup reference is her face.

She’s the ultimate alien.

She’s the ultimate alien! I think that’s why I’m so obsessed with alien vibes.

Okay, let’s finish with some "this or that” questions. This or that: ankle boots or sneakers?

Sneakers.

Jeans or dresses?

Dresses.

Vintage or new?

Vintage!

Leather or lace?

It depends on my mood.

Lipstick or highlighter?

Highlight.

Next: Check out our shoot with the stars of Pen15.

Photographer: Felisha Tolentino

Photo Assistant: Alexander Gay

Stylist: Hillary Comstock

Market Editor: Lauren Eggertsen