Shiloh Jolie-Pitt's Style Transformation, From Comfortable Classics To Punk-Rock 'Fits

Raising a child while having all eyes on you is certainly no easy task — let alone raising six of them. Yet, Hollywood stars and former spouses Angelina Jolie and Brad Pitt have managed to do an incredibly impressive job with children Maddox, Zahara, Shiloh, Pax, Knox, and Vivienne. All of the Jolie-Pitt siblings seem to be on paths that allow them to nourish their hearts and explore their wishes, all with the support of their famous parents. Shiloh Jolie-Pitt, the first biological child of the two stars, has captivated public interest since the day she was born, and not much has changed since.

Over the past decade, Shiloh has grown from a toddler to a teen in one of the world's most probing spotlights, and with that, her style has certainly changed plenty. Once known for explicitly wearing boys' clothes, Shiloh has been exploring more feminine pieces in the past couple of years (along with edgy, punk-inspired 'fits), allowing her style to flow naturally between traditional gender expectations. And while her mother and father are well-known style icons, there's no denying that Shiloh Jolie-Pitt is exploring fashion in an authentic way that is inspiring plenty of people worldwide.

On May 27, 2006, Angelina Jolie gave birth to Shiloh Nouvel Jolie-Pitt, her and Brad Pitt's third child at the time. The whole world was excited to see what the offspring of two of the most famous Hollywood stars would look like, and baby pictures of Shiloh ended up being sold to People for more than $4 million — an unprecedented price at the time.

When Shiloh was a baby, we got to see her wear mostly comfortable clothes as she traveled the world with her parents and siblings. "Shi's so full of light and love, she's just a little honey, and very, very funny," Jolie revealed in a 2007 interview (via People). "I think I'm recognizing some of myself in that one — she's going to be a little bit of trouble!" In 2020, Angelina Jolie opened up to Time about what becoming a mother meant to her, explaining that love wasn't the difficult part. "It wasn't hard to dedicate myself to someone and something greater than my life," Jolie said. "What was hard was knowing that from now on, I needed to be the one to make sure everything was okay. To manage it and make it work. From food to school to medical. Whatever would come. And to be patient." Of course, as Shiloh was just a baby, she couldn't pick her clothes just yet, so her early style can only be attributed to her parents.

Once Shiloh Jolie-Pitt began growing, a subtle change in her style instantly became noticeable. Back when her parents were picking her clothes, they would usually put her in comfortable, gender-neutral pieces, as if wanting Shiloh to have a blank canvas to start from. Once Shiloh turned 2 in 2008, she began leaning toward pieces most often found in the boys section — as graphic tees and cargo pants seemed to be some of the toddler's favorite choices.

Shiloh's style preferences became even more evident when she was photographed next to her sister Zahara Jolie-Pitt, who always loved feminine and colorful clothing. With Zahara being only a year older, their style differences became even more significant. Even though Shiloh had no idea at the time, she was in the early stages of becoming a trailblazer for Hollywood kids when it came to authenticity. And as the toddler became a topic of public interest and the world debated what Shiloh should or shouldn't wear, her parents allowed her to have full control over expressing herself, something every parent out there can definitely take some notes from.

Shiloh Jolie-Pitt turned 4 in 2010, and by then, anyone who had been keeping up with the Jolie-Pitts knew Shiloh loved mixing masculine style elements into her outfits. "She likes to dress like a boy. She wants to be a boy. So we had to cut her hair. " Jolie revealed in 2010 in an interview with Vanity Fair, per the Daily Telegraph. "She likes to wear boys' everything. She thinks she's one of the brothers." At the time, we got to see Shiloh in numerous fun pieces, the memorable of the period being the red nutcracker-inspired jacket and the T-shirt with a stitched-on red-and-blue tie.

Jolie has always been open about how much she admires Shiloh's approach to fashion. "I think she is fascinating, the choices she is making. And I would never be the kind of parent to force somebody to be something they are not," Jolie told Reuters of Shiloh in 2010. "Children should be allowed to express themselves in whatever way they wish without anybody judging them because it is an important part of their growth." In her interview with Vanity Fair, the Hollywood star revealed the family's take on Shiloh's style. "Shiloh, we feel, has Montenegro style," she told the outlet, adding, "She dresses like a little dude. It's how people dress there. She likes tracksuits, she likes [regular] suits." In 2012, Shiloh turned 6, and by then, it was clear that she was going to be unapologetically herself, regardless of whether her choices fit in or stood out.

Around the age of 8, Shiloh Jolie-Pitt began attending movie premieres with her parents. In 2014, she accompanied her father, Brad Pitt, to the premiere of "Unbroken," a movie directed by her mother, Angelina Jolie, who couldn't attend due to having contracted chickenpox. Alongside Pax and Maddox Jolie-Pitt, Shiloh posed on the red carpet in a classic suit, showcasing that she truly loves taking fashion inspo from her older brothers. With her short hair styled in a deep side part, Shiloh ensured all eyes were on her bold fashion choice.

Shiloh's casual street style at the time involved lots of grays and blacks, loose-fitting pieces, and few accessories. The older she grew, the more evident her confidence in rocking tomboy fashion became. And as she grew into loving oversized and neutral pieces, her sister Zahara continued experimenting with colorful ensembles, further showcasing that Jolie and Pitt allowed all of their kids — as they changed through the years — to experience fashion in the way it's meant to be experienced: as a personal journey of self-discovery.

One of Shiloh Jolie-Pitt's most memorable looks from 2015 is undoubtedly the outfit she wore to the Nickelodeon's Choice Awards. She attended the event with her mother, Angelina Jolie, and her sister, Zahara Jolie-Pitt — and the three of them certainly had plenty of fun during the girls' night out. In fact, when Jolie won in the category "Favourite Villain" for her portrayal of Maleficent in the eponymous movie, Shiloh and Zahara were more excited than we'd ever seen them.

For the occasion, Shiloh stayed true to herself by rocking a funky graphic tee, beige shorts, sneakers, and a gray zip-up hoodie. In her acceptance speech, Jolie made sure to empower those who feel like they don't fit in. 'When I was a kid I was told — like Maleficent — that I was different. But then I realized something: different is good," the Hollywood star explained (via Daily Mail). "So maybe you don't fit in. Be yourself. And when someone tells you that you are different, just smile and hold your head up, and be proud." With Jolie (who has an arsenal of amazing style secrets) as her mother, it's certainly not surprising that Shiloh wasn't forced into a box; instead, she was praised for trusting herself — as she should be.

2016 marked a difficult year for the family, as Angelina Jolie and Brad Pitt separated, which led to Jolie filing for divorce, stating irreconcilable differences as the reason. This was undoubtedly a difficult change for all of the children. In a 2020 interview with Vogue, Jolie reflected on her decision to end things with Pitt. "I separated for the wellbeing of my family. It was the right decision. I continue to focus on their healing," the actor admitted. "Some have taken advantage of my silence, and the children see lies about themselves in the media, but I remind them that they know their own truth and their own minds. In fact, they are six very brave, very strong young people."

Even though the family dynamics were changing, Jolie ensured her children were happy and nourished their interests. A source for Us Weekly revealed in 2016 that Shiloh is a big fan of photography. "Shiloh is very interested in photography, and Angelina asked to look at some of the vintage cameras," the source said. "Angelina inspected the cameras from many different angles and was asking questions. Shiloh was listening intently and paying close attention." Between 2016 and 2018, Shiloh's style continued evolving — she cut her hair even shorter, frequently rocked a brown statement necklace, and continued exploring traditionally masculine fashion pieces. Whenever spotted, Shiloh seemed happy and confident, and it was clear that she was about to enter teenhood as a young person who isn't afraid of showing what she likes — whether it's her hobbies, her clothes, or the path she wants her life to take.

In 2019, Shiloh Jolie-Pitt turned 13, and with that, she had officially entered teenhood. As a teen, she grew even more comfortable in her skin, and that was clear as day during her red-carpet appearances alongside her mother and siblings.

Angelina Jolie took her children to the "Maleficent: Mistress of Evil" premieres that year, and each time the family hit the red carpet, we couldn't help but notice how unique each of the siblings' styles were. For the premiere in Rome, Italy, Shiloh went with navy pants and a fun black varsity jacket with subtle gold detailing. Zahara Jolie-Pitt, on the other hand, went with a deep-green dress, and Jolie stunned in a sparkly black gown. Each three of the ladies looked incredible, in their very own way. And it was around this time that the world began realizing that Shiloh was growing into a fashionista in her own right. While she may not have been rocking pinks and skirts, Shiloh was giving a voice to those who enjoy more androgynous fashion, showcasing that her preference for pieces from the boys' section didn't mean she wasn't fashionable. After all, much of what fashion is about is confidence, and Shiloh never lacked in that department.

A more dramatic shift appeared in Shiloh Jolie-Pitt's style during the COVID-19 pandemic, as the Hollywood teen began embracing a more feminine side of her. In fact, at the Los Angeles premiere of "Eternals," a Marvel movie Angelina Jolie stars in, Shiloh went shopping in her mom's closet. The 15-year-old rocked a Dior dress previously worn by her mother in 2019 — and we have to admit Shiloh wore it just as well as Angie. The Hollywood star revealed to E! News that she loves it when her children decide to wear something of hers. "I'm like, 'Oh my god, wear it and wear it better than me! Take it, it's your turn,'" Jolie admitted. "I'm that mom."

At the age of 15, Shiloh had also fallen in love with a new hobby — dancing. And while we can't claim it for sure, we have a feeling that dancing also majorly influenced the change in her style, allowing her to explore all facets of herself. "Shiloh is a typical 15-year-old and she's expressing herself in so many ways," a source revealed to In Touch in 2021. "Her main love right now is dance, and she's really good at it. She loves that she can feel the music, let go and be free, which is super important. She likes all styles of dance but hip-hop and freestyle are her favorites." With a new hobby to inspire her, Shiloh was now exploring colorful fashion, new silhouettes, fun hairstyles, and makeup — all at her own pace.

By 2022, Shiloh Jolie-Pitt became known for her dancing, and choreographer Hamilton Evans even posted multiple videos of her performing dance routines he created. Of course, because practice became a major part of her life, Shiloh was mainly spotted wearing comfortable pieces that allowed her to move freely and weren't constricting her while dancing.

During an interview with Entertainment Tonight in 2023, Brad Pitt admitted just how proud Shiloh makes him, noting that he has no idea where her dance talent comes from. "It brings a tear to the eye, yeah. [She's] very beautiful. I don't know where she got it from. I'm Mr. Two-Left-Feet here," Pitt said. "I love when they find their own way, find things they are interested in and flourish." Even though her parents separated, it has been clear that both of them have supported Shiloh's journey in any way they can — especially her desire to dance. "Angie's very encouraging of that," a source revealed to Life & Style in 2023. "She wants all the kids to explore their creative sides and hear from talented actors and actresses directly what it's like to work in the biz, how they got their start and so on and so forth." Regardless of whether dance continues to be a major part of Shiloh's life in the future or it simply remains an interest only during her teens, there's no denying that it allowed the young star to explore and embrace a new side of herself.

Shiloh Jolie-Pitt has always had a preference for shorter hair, and toward the end of 2023, she entered her buzz-cut era — adding another style to her stunning hair transformation. With her buzz cut, she closely resembled her mother in the late '90s, when the Hollywood star embraced a bold buzz cut herself. We don't doubt for a second that chopping her locks off was entirely the 17-year-old's wish, as her parents have always encouraged her to go through with what she wants. "[Angelina] knows Shiloh is a woman now and can make her own decisions," a source told Life & Style, speaking of Shiloh's plans to move in with her father.

While Angelina Jolie and Brad Pitt have gone through a difficult separation, both stars have ensured their children remain their priority. "She's humble, has a lot of empathy for people in need and is wise beyond her years," a source revealed to Life & Style in 2024. "A lot of that credit goes to Brad and Angie. They tried to give her a normal childhood and make sure she felt protected." Today, with her buzz cut and love for casual yet cool fashion, Shiloh is one of the most well-known Hollywood kids inspiring others to walk their own path. Even though Shiloh is still very young, her style transformation already serves as an example of how to defy conventional gender norms, proving that fashion is truly a world everyone can feel comfortable in if only they allow themselves to make authentic choices.