The Stunning Hair Transformation Of Shiloh Jolie-Pitt

From the moment she was born as the first biological child of Hollywood's biggest at-the-time power couple, Angelina Jolie and Brad Pitt, Shiloh Jolie-Pitt has been under the tough eye of the spotlight. As the offspring of one of the world's most famous celebrity duos, Shiloh's every move, every look, and every appearance has been analyzed in detail across the world. From her earliest years, the public has eagerly watched as she grew from an adorable infant into a confident and stylish young woman, mirroring the charisma of her A-lister parents.

As she grew, so too did her sense of self and style, evolving from the little tomboy girl effortlessly rocking a chic bob to the confident teenager embracing bold and daring hair transformations. And somewhere along the way, young Shiloh has emerged as a symbol of individuality, defying societal norms and expectations with her authentic sense of self-expression and complete self-acceptance. In fact, both of her parents are aware of how inspiring Shiloh's approach to life is."Brad is so proud of Shiloh and who she has become," a source told Entertainment Tonight. "He loves that she always stays true to herself and is so good to her brothers and sisters." As we go into the various stages of Shiloh's hair evolution, we can't help but notice that each hairstyle choice conveys a message about her personality and who she sees herself as — even if the look is just temporary.

2007-2009: Shiloh rocks a chic little bob as a toddler

In the years following her birth, everyone was curious about who Shiloh Jolie-Pitt would take after more — Angelina Jolie or Brad Pitt. With her naturally light blond hair, some assumed she inherited her father's features, while others saw strong echoes of Jolie's childhood — believe it or not, the actor was naturally blond as a child.

Between 2007 and 2009, Shiloh sported a chic little bob that perfectly complemented her face. The hairstyle was both adorable and practical, and it allowed her beautiful blond color to shine. At the time, Jolie gushed about her daughter's personality: "Shi's so full of light and love," she said in an MSN interview. But she also predicted a mischievous streak when she admitted, "I think I'm recognizing some of myself in that one — she's going to be a little bit of trouble" (via People). Despite the early speculation about her appearance, Shiloh's parents embraced her uniqueness wholeheartedly. Jolie once remarked on her daughter's resemblance to Pitt, humorously noting that she might be the "outcast" in the family due to her blond hair and blue eyes (via TODAY). At the time, the two stars hadn't welcomed their twins, Vivienne and Knox, yet.

Early on in her life, it became clear that Shiloh wouldn't be put in any traditional molds, and her parents fully let her explore her style, including her hair. Pitt himself shared an anecdote about Shiloh's preference for names, revealing that she may be young, but she already knows what she wants — and she makes sure she lets everybody know. "She only wants to be called John. John or Peter. So it's a Peter Pan thing," Pitt revealed on "The Oprah Winfrey Show" at the time.

2010: Shiloh shows off a deep side part as her hair gets a tad shorter

In 2010, Shiloh Jolie-Pitt's hair underwent a very subtle transformation, reflecting the fact that she was growing up. While still maintaining her signature bob hairstyle, the four-year-old opted for a slightly shorter look with fun face-framing side bangs. Whether out and about with her siblings and mother in New York City or jetsetting around the world, Shiloh's hair was blond with beautiful, natural sunkissed highlights and subtle layers. And yes, when we say she picked it herself, we mean it — Angelina Jolie has opened up about her daughter's style preferences over the years.

"It's not my choice," Jolie revealed in 2010 to Stylist (via Mirror). "I have a very strong-willed four-year-old girl who tells me what she wants to wear, and I let her be who she is. People look at kids and think they should wear certain types of clothes. I think children should wear what they want and express themselves. Shiloh cried and said: 'Please cut my hair off; I don't want to have long hair.' I'm not going to leave it long because somebody thinks I should. I want to do what's in her heart, and what's in her heart is to dress like that. I think it's beautiful."

The actor has always been known for advocating for children's right to self-expression, and through Shiloh's bold and confident decision to embrace a shorter hairstyle (even though she might not have been aware of it at the time), the four-year-old became a very young trailblazer for rocking whatever you like.

2011-2013: Shiloh is all about her signature bob and deep side part

Between 2011 and 2013, Shiloh Jolie-Pitt continued to rock her iconic bob hairstyle with a side part. Apart from her hair growing a bit longer, she remained firm in her fashion expression. During a sighting in New York City in 2011, Shiloh was spotted rocking her hair in a relaxed and slightly messy hairstyle while wearing a fun shirt with a tie printed on it. "[She dresses] like a little dude. Shiloh, we feel, has Montenegro style," Angelina Jolie revealed (via Vanity Fair). "It's how people dress there. She likes tracksuits; she likes [regular] suits. She likes to dress like a boy. She wants to be a boy. So we had to cut her hair. She likes to wear boys' everything. She thinks she's one of the brothers."

Through her fashion choices and her hairstyle, Shiloh confidently defied societal expectations as she embraced her individuality. Of course, as a seven-year-old in 2013, she was simply navigating her own journey of self-discovery, not knowing that the whole world was watching and that she was inspiring many. However, even as a seven-year-old, we're sure she realized that other kids her age would follow a certain style — one that she simply wasn't drawn to.

2014: Shiloh owns a more traditionally masculine haircut

The older she got, the more confidence in her look Shiloh Jolie-Pitt gave us, and in 2014, she rocked an even shorter haircut. If it wasn't clear by then, now everyone knew that Angelina Jolie and Brad Pitt's eight-year-old was all about rocking looks typically associated with boys. Her bold choices extended beyond her haircut, as she made appearances at red carpet events dressed in suits rather than dresses, boldly posing with her brothers. One such occasion happened in December 2014 when she attended the Los Angeles premiere of the movie "Unbroken" alongside her father and her older brothers, Maddox and Pax. Just like them, Shiloh also rocked a black suit and tie, and her locks were pushed back into a sleek hairstyle.

Over the years, Jolie has emphasized the importance of nurturing her children's individuality and allowing each of them to explore their identities freely. "We're supposed to help them figure out who they are," she told People. "And you can't figure out who they are if you don't enthusiastically develop with them." While this may seem more socially accepted now — even though there's still a long way to go — we have to remember that Jolie and Pitt were one of the first celebrity parents who publically talked about the significance of embracing their children's self-expression. And judging by Shiloh's confidence, the two stars managed to create an environment of acceptance and understanding.

2015-2016: Shiloh's hair is super sleek and short

During 2015 and 2016, Shiloh Jolie-Pitt's hair became sleek and short, and she continued to change her style. As she navigated her preteen years, the distinction between Shiloh's tomboy aesthetic and her one year older sister Zahara's more fashion-forward approach to style became increasingly apparent. While Shiloh favored a more casual look when it came to hair and clothing, Zahara displayed her love for flashy fashion. An example of this was the 2015 Nickelodeon Kids' Choice Awards, which Shiloh and Zahara attended with their mother, Angelina Jolie. While Zahara went for a classy white sweater, straightened hair, and pearl earrings, Shiloh rocked a graphic tee and a zip-up hoodie with her signature casual bob. The difference in their choices only highlights the diverse range of styles that can emerge within the same household if children are simply allowed to explore style preferences early on.

"I don't think it's for the world to interpret anything," Jolie told The Daily Mail. "She likes to dress like a boy and wants her hair cut like a boy and she wanted to be called John for a while. Some kids wear capes and want to be Superman, and she wants to be like her brothers. It's who she is. It's been a surprise to us and it's really interesting, but she's so much more than that — she's funny and sweet and pretty. But she does love a tie..." 

2017-2018: Shiloh cuts her hair super short and loves it

Throughout 2017 and 2018, Shiloh Jolie-Pitt showcased her individuality and masculine style even more. As she entered her tween years, Shiloh opted for an even shorter pixie haircut, further clarifying that she prefers looking up to her brothers for style inspiration. 

Her bold, masculine-inspired style choices were evident during notable public appearances, such as the Premiere of GKIDS' "The Breadwinner" in October 2017 and the 2018 National Board of Review Awards Gala. At these events, Shiloh captured attention with her fashion sense, pairing her short, slightly messy hairstyle with classic suits. Her attire continued to defy traditional gender norms. While the public consistently commented on her appearance, Shiloh seemingly lived a happy and authentic life. And even though her parents were going through a breakup and divorce — which surely couldn't have been easy for her and her siblings — being allowed to be her authentic self surely helped her deal with harder times.

2019: Shiloh keeps it easy and simple

In 2019, Shiloh Jolie-Pitt transitioned into her teenage years, and with that, she began accompanying her mother to even more industry events. One memorable fashion and hairstyle choice came in October 2019, when she joined her mother at the European premiere of "Maleficent: Mistress of Evil" (a movie that would go on to inspire an entire villain makeup trend). Shiloh exuded cool sophistication in an edgy black jacket, effortlessly complemented by her deep-side part and perfect slicked-back hairstyle — providing a polished and shiny finish to the look.

By now, it was clear that Shiloh's hair was an integral part of her overall look. "Knowing our true self is a very important question for all of us. Especially a child," Angelina Jolie told Harper's Bazaar at the time. "I think kids need to be able to say, 'Here's who I am and what I believe.' We can't prevent them from experiencing pain, heartache, physical pain, and loss. But we can teach them to live better through it." As 13-year-old Shiloh began navigating the complexities of adolescence under the spotlight, she was surely more aware of the fact that she wasn't really living a completely normal life. However, completely owning her self-confidence has served as an inspiration to so many young teens worldwide. With each public appearance, she continued to rock beauty and style on her own terms.

2020-2021: Shiloh has more fun with her hair and explores a more feminine look

During the years of the pandemic, Shiloh Jolie-Pitt continued to explore new facets of her identity. Embracing a more playful and traditionally feminine approach to her look, Shiloh made a slight departure from her previous tomboy aesthetic. With her hair a tad longer than usual, she seized the opportunity to experiment with various updos, adding a bit of sophistication to her style. In 2021, Shiloh made appearances at the "Eternals" UK Premiere and the Rome Film Fest, and for both, she decided to go with stunning updos, one of which even featured intricate braids. 

"I am curious about all the different aspects of who they are. And I want to be there to support and develop all the different aspects of who they are," Angelina Jolie admitted (via TODAY). Jolie's support and encouragement clearly allowed Shiloh to explore a new aesthetic. By now, her family certainly knew that Shiloh was very strong-minded and would only rock things that she genuinely liked — and the feminine aesthetic had started to pique her curiosity. For both events, Shiloh rocked stunning fashion ensembles, and Jolie admitted that her daughters are now at an age when they frequently raid her closet. "I'm like, 'Oh my god, wear it and wear it better than me! Take it, it's your turn,'" the actor told E! News.

As Shiloh's style continued to evolve, she also found inspiration in her sister Zahara. "Shiloh loves music, dance, acting, and lately, thanks to her sister Zahara, fashion. It wasn't always like that, but now she loves dressing up in her mom's clothes," a source told Life & Style in 2021.

2022-2023: Shiloh rocks her hair up before buzzing it

Once Shiloh Jolie-Pitt turned 16 in 2022, she delved deeper into her passions, with dancing emerging as a significant part of her life. Displaying talent and dedication, Shiloh's love for dancing became increasingly evident as she worked hard on her skills in classes and workshops. "Shiloh loves dancing," a source told US Weekly. "She's seriously talented and has been going to these classes for a few years now. ... The teachers are all very impressed with her and say the sky's the limit if she wants to take it to the next level, and Shiloh may just do that." Recently, many of Shiloh's appearances in dance videos on social media showcased her with her hair styled up, a practical choice that allowed her to focus on dance. While Shiloh remains casual when it comes to her style, she has decided to keep her locks longer, at least for now.

According to the US Weekly source, Angelina Jolie and Brad Pitt continue being supportive and encouraging, allowing Shiloh to explore her passion for dancing at her own pace. "They'd have no issue if she wants to turn pro, but they're not pushing it on her by any means," the source said.

2024-present: Shiloh's pink buzzcut signals her punk-style era

In a bold and daring move that captured everyone's attention, Shiloh Jolie-Pitt decided to go with a striking new look: a vibrant pink buzzcut — a hairstyle known for quite a few benefits. Embracing the punk-inspired aesthetic, Shiloh's edgy hairstyle gave us a youthful vibe in the best way possible. In fact, we can't help but immediately think of all of Angelina Jolie's rebellious phases.

"I'm that mom that if I see your rebellious spirit, it warms me. And I think, 'Good for you, you got fire,'" Angeline Jolie told People in 2021 (via TODAY). The star fully supported Shiloh's decision to embrace her edgy-style journey. With six children under her wing, Jolie exemplified the importance of nurturing individuality and allowing her children to always have the freedom to express themselves authentically. In a world where societal norms frequently dictate appearance, Shiloh's fearlessness and individuality are a reminder that true beauty is all about what you like — and it never should be about what others think.

As Shiloh continues to live her young adulthood and explore her evolving sense of identity, there's no denying that all eyes will be on her. And knowing that she's growing up in the eye of the public doesn't come easy to her parents. "Brad doesn't want her growing up so fast, but he's proud to see her on red carpets. It's been a confidence boost for Shiloh," a source told Life & Style. "Of course, he worries about the effect of Hollywood on all his kids, but he does trust Angie's instincts in this area." As for us — we simply can't wait to see where Shiloh's hair journey takes her next!