The Stunning Style Transformation Of Willow Smith

For some, Willow Smith may still be a nepo baby who has found her way to fame thanks to her parents, Hollywood stars Will Smith and Jada Pinkett Smith. However, anyone who takes a closer look at Willow's art will know that she is so much more than just the girl who whipped her hair back and forth at the age of 10. Today, Willow not only has six albums under her belt, but she is also one of the most stylish and authentic celebrities of her generation.

"My style is who I am all the time," she told Teen Vogue in 2014, "and who I am always changes." More than a decade later, this is just as relevant for the singer, who keeps reinventing her aesthetic while always ensuring she remains true to herself. For someone who is only in her mid-20s, Willow's fashion journey is incredibly impressive and undeniably inspirational. So, while we're excited to see where her style goes in the future, we invite you to take a trip down Willow Smith's fashion memory lane with us!

Willow Smith was born on October 31, 2000, and the fact that she was born on Halloween — the one night that dressing up knows no limits — was major foreshadowing for her style. In fact, at the time, nobody could predict that young Smith would become a little fashionista in the 2000s at such a young age, but whenever she attended industry events with her parents, Smith's quirky and fun style took the spotlight. From glamorous to casual — there wasn't a style the youngster couldn't pull off.

"When I was seven, there were these white, black, red, and blue checkered patent leather boots that I loved so much," Smith told W in 2019. "They had a tiny square heel, and those boots were my favorite thing. But I've always lived in woodsy places, and those boots did not survive. Too pretty to live!" While her fashion choices were changing on the daily, one thing was quickly clear — Smith had undeniable confidence that made anything she wore stand out — and she hadn't even turned 10 yet!

In 2010, Willow Smith — who was only 10 at the time — released her debut single "Whip My Hair," which instantly became a hit across the globe. A year later, Smith explained just what the song meant to Teen Vogue. "Whipping your hair means not being afraid to be yourself," the young artist said. "If people don't like you, then bunck them, you know?"

With the kick-off of her music career, Smith's style became even more fearless. The gray jumpsuit and yellow leather armpiece she wore to the 2010 American Music Awards was styled by Brea Stinson, and this was something we could have easily imagined fashion-risk-taking stars like Lady Gaga would pull off — but a 10-year-old? It's safe to say we were all surprised by Smith's approach to fashion. The young star was figuring out her personal style and being very adventurous while doing so. "I wear anything I feel like," she said in the 2011 interview with Teen Vogue. "If I want to put on a pair of Converse with a pencil stuck through them, I will."

2012 marked a surprising year when it came to Willow Smith's appearance, as the young star decided to go for a buzz cut — saying goodbye to the hair that became such a major trademark of hers, thanks to her 2010 debut single. In fact, this moment is definitely a strong contender for the most drastic celebrity hair changes in pop culture history. With her fresh new hairstyle, Smith shed some of that childhood image — and even though she was just about to enter her teens, everyone could tell that she had matured very quickly, and her sense of style was following suit. And yes, this was just the beginning of Willow Smith's stunning hair transformation.

"The energy that your hair holds through your whole life, all of your sadness and your happiness and your confusion, your hair is on you forever," Smith reflected many years later, thinking back on the decision to chop off her locks (via Allure). "And when you shave it off, you're kind of naked. You're kind of like, you need to be new now." And as she headed into a new era of her life, Smith was trying to figure out who she was in front of the entire world.

While Willow Smith was undoubtedly a stylish kid in the 2000s, it wasn't until she entered her teens that she actually became a fashion icon that fellow teens (as well as grown-ups) across the world looked up to. In fact, it's impossible to think of Tumblr's cool-girl era without Smith, for whom plaid button-ups and grungy fashion were an everyday look.

"I like to go to places with my high-fashion things where there are a lot of cameras, so I can just go there and be like, 'Yep, yep, I'm looking so sick,'" Smith said in 2014 (via Glamour). "But in my regular life, I put on clothes that I can climb trees in." In a candid conversation with Wonderland Magazine that year, Smith elaborated on what personal expression through style means to her. "Flexibility with yourself and with your looks shows self-confidence," the artist told the outlet in 2014. "You're willing to paint on your canvas with whatever comes from within you."

When asked to describe her aesthetic the following year, Smith said, "High-fashion nomad. I could literally climb a mountain and survive a couple nights in nature," she said (via Billboard). "If you're an artist, the way you dress also gives people a vibe of how your music is and your personality." In 2015, Smith released her debut studio album "Ardipithecus," which included her hit "Wait a Minute!" — a song that blew up on social media in the early 2020s.

2016 was a major fashion year for Willow Smith. Not only was she one of the most well-known teen style icons in Hollywood — but she also made her Met Gala debut. For those who don't know, the Met Gala has rules all attendees need to follow — and no invitation means no attendance. For the milestone, Smith wore a stunning Chanel three-piece set that perfectly showed off both her quirky and elegant sides simultaneously. And yes, in 2016, Smith became Chanel's ambassador, adding plenty of unexpected edginess to the brand. "Being a young African-American woman with dreads, it blows my mind that I'm a Chanel ambassador. Like, how am I a Chanel ambassador," Smith told Teen Vogue as their cover star in April 2016. "All I can do from here is continue to shift paradigms and continue to push the envelope further and further. But I am doing it every day just by being myself."

Furthermore, the young star explored how fashion doesn't define her — and how she's always ready for change. "I have some cool shoes on and I wear crazy eyeliner, but it's really all about emulating the colors you feel inside," Smith said. "A lot of clothes are cute, but after you buy the Yeezy shoes, after you get your hair done with a weave, you're still the same person. I feel like more and more kids are starting to realize this."

In 2017, Willow Smith released her second studio album "The 1st," and with it, she leaned a bit more into the pop-rock genre while staying true to her soul roots. Now a 17-year-old who had already achieved so much, Smith's confidence was evident from a mile away. And for her fashion, that meant exploring more of a rockstar aesthetic, often experimenting with a variety of funky accessories. While Smith's style was difficult to put into a box — we can certainly say that her style was androgynous, but it wasn't minimalist.

"I'm a Black female in the 21st century," the star told Refinery29 in 2017. "My favorite color isn't pink; it's black. I'm not obsessed with getting married or having kids. Gender norms put people in boxes and don't allow them to really get to their full potential as a human being. Slowly but surely, dudes are starting to wear nail polish and become more in tune with their feelings. Change is happening, and it's very exciting." Apart from her clothing, it was clear that Smith's hair and makeup also played a major role in the picture she was painting of herself — and the way she was embracing and honoring her heritage.

Willow Smith turned 18 in 2018, and with that, she definitely said goodbye to some of the colorful fashion she was drawn to when she was younger. While Smith had been rocking predominantly black fashion for years, by 2018, it had undeniably become her thing.

One of her most memorable 2018 looks was the sheer black skirt and deep-cut vest combo the star wore for the Christian Dior Haute Couture Spring/Summer show. While it was a bit more minimalist than what we were used to from Smith, she added her signature twist to the look with her makeup. In particular, it was the graphic white eyeliner on her bottom lashline that made us all want to buy one and try the trend out immediately! In fact, Smith was one of the few celebs who shaped the way the bold graphic liner look evolved in the late 2010s and early 2020s.

By 2019, it was clear that Willow Smith was one of the most authentic young stars on the scene, at least in terms of her style and music. That year, the singer released her third studio album "Willow" and revealed that a lot of her fashion inspiration comes from what her mother Jada Pinkett Smith wore in the '90s. "My mom is now very feminine, and I'm not really into heels, makeup, or any of that. But my mom, in her youth, influenced the androgynous way I dress," Willow admitted to W in 2019. "Back then she was a tomboy ... She was in baggy jeans and T-shirts, which is the '90s boyish look that's now coming back big-time. That era of my mom's dressing will always be inspiring to me." Similarly, she also admitted that her brother Jaden Smith influenced her style heavily when she was younger. "I wanted to dress like him, be like him, hang out with him." 

As far as her 2019 fashion inspiration goes, Willow noted that the 2005 neo-noir classic "Sin City" served as a major source of inspiration. " ... I try to be a 'Sin City' girl. Especially when I go to an event, I try to emulate one of the women in that film," Willow shared with W. "I wear everything dark, put on my Dr. Martens boots and an amazing trenchcoat that is made by Max Mara, I think, and is wonderfully oversize." The musician's looks at the time revolved around unique silhouettes and fun pops of color, often achieved through makeup. In fact, Willow wasn't one to shy away from bold makeup looks, and not even teal lipstick could scare her.

During 2020 and 2021, Willow Smith remained true to her style, and a major reason why expression through fashion is so important to her became clear in her 2020 conversation with Marie Claire. "When someone has the courage to stand up and say, 'I'm different and that's okay,' or when someone chooses to stand up and say whatever it is that's true to them, without fear, that gives me hope," she admitted. And looking back at Willow's career over the past decade, it certainly seems as if part of standing up for herself also meant showcasing her style to the entire world — whether they approve of it or not. In 2021, the artist released her fourth studio album "Lately I Feel Everything," and with it, she explored the genre of punk rock even more.

Her style continued evolving into an even edgier sphere, especially since the musician was once again rocking a buzz cut. On a 2021 episode of "Red Table Talk" — a talk show she often hosts with her mother Jada Pinkett Smith and grandmother Adrienne Banfield-Norris — Willow revealed that it wasn't uncommon for her to go to work and find that the hairstylist didn't know how to approach her hair. "The person that was supposed to come do my hair came, looked at it, and tried to do something to it, tried to touch it ... I could tell that they were just like, 'I don't know what I'm doing,'" she admitted on the episode. "That anxiety, looking at them in the mirror not knowing what to do with my head, made me feel like, 'I'm gonna take the reins on this,'" that musician admitted. "I basically did my own hair for that really high-fashion shoot. That should never be happening."

When the COVID-19 pandemic ended, Willow Smith was in her early 20s, and she finally seemed ready to embrace a bit more glamour. Now, don't get us wrong — her looks were far from conventionally glamorous fashion. Instead, they were alternative, edgy, and very goth-punk inspired.

Nevertheless, the musician rocked them to traditionally glamorous events, like the Vanity Fair Oscar Party. In 2022, Smith showed up to the cult Hollywood soirée in a bra top that featured eye-catching embellished sleeves and a pair of high-waisted black pants. These two alone would be way too dramatic for some stars, but Smith has shown she can pull off way more. In fact, she didn't stop there — she added a statement necklace, earrings, a chunky belt, motorcycle gloves, and slim '90s sunglasses to the look. Sounds like it would be all over the place, right? Well, somehow, it looked incredibly stylish on Willow Smith!

As her mid-20s were approaching, Willow Smith was exuding a confidence we rarely get to see in young celebrities who grow up in the spotlight. "I represent certain parts of traditional beauty, but then there are other parts that I don't represent," she told Allure in 2024. "My legs are never shaved. I always have hairy-ass armpits like, I'm brown, my hair is nappy. That's why I think I straddle a very interesting position in the beauty standard world."

In 2024, Smith released her sixth album "Empathogen," but she also branched out into working behind the fashion scenes as her collection with Moncler had its debut. When asked to describe the collection, Smith said, "Minimalism and utilitarianism. Femininity and masculinity. Black and white. Bringing juxtaposing ideas together in an elegant way is something that really excites me, and I wanted to explore that in this collection" (via WWD). Furthermore, Smith stressed the importance of fashion that looks cool but is also adventure-proof. "I'm incredibly passionate about the outdoors and exploring this magnificent earth. I imagine these clothes effortlessly transitioning from nighttime camping to high-fashion eveningwear," the singer added. When Hypebae asked her to describe her style at the age of 24, Smith replied, "Modern minimalistic with an artistic edge, often wearing natural colors or earth tones and embracing unique shapes." Of course, looking back at her style at the beginning of her career, the change it went through is undeniable.

Today, Willow Smith is just as much of a style icon as she is a talented musician. Over the years, she has managed to use fashion not only as a tool to express herself but also to become closer to her fans, who have cherished her authenticity and boldness above all. So when Smith showed up to the 2025 Grammy Awards red carpet (she was nominated in two categories for her 2024 album "Empathogen") in a bedazzled lingerie set by Fleur du Mal and floor-length oversized blazer by McQueen, our jaws collectively dropped.

Sure, we've seen celebs rock lingerie as fashion, but Smith managed to make it both sexy and sophisticated, edgy and ethereal, but most of all, so simple yet incredibly impactful. Many have tried to master the art of fashion over the years, but if you ask us, Willow Smith was simply born with it.

Now, if you care for some more nepo baby fashion, check out the stunning style transformation of Hailey Bieber!