How Shiloh Jolie-Pitt's Hair Has Changed Through The Years

In May of 2006, the Los Angeles Times declared, "The Wait Is Over: Angelina Gives Birth to a Girl." The headline, of course, was in reference to Hollywood icon Angelina Jolie, who had just welcomed her first biological child with fellow actor Brad Pitt. Weeks later, baby Shiloh Jolie-Pitt graced the cover of People magazine. Fans were instantly enamored with the angel-faced newborn. At just a few weeks old, little Shiloh was already a celebrity.

In 2010, Jolie told Vanity Fair that Shiloh was, "Goofy and verbal, the early signs of a performer." With so much star quality, it's no surprise that Shiloh is one of the most talked-about kids in Hollywood. Like most young celebrities, Shiloh has received her fair share of unwanted media attention. From an early age, her short hair and gender non-conforming clothes were the subject of numerous cruel, invasive tabloid stories. But despite these challenges, Shiloh seems comfortable with who she is — and she's not afraid to show her style to the world. Throughout the years, Shiloh has delivered a dazzling assortment of ever-changing hairstyles. Let's take a look back at her iconic hair journey.

Blonde like her papa

By the time Shiloh Jolie-Pitt arrived in 2006, Brad Pitt and Angelina Jolie were already parents to two adorable little ones. Their eldest, Maddox, was adopted from Cambodia in 2002, followed by Zahara from Ethiopia in 2005. The famous family was no stranger to making headlines, but Jolie's pregnancy was their biggest news yet. For fans, the image of a tiny human bearing Brangelina's combined genetics triggered a whole new level of obsession. A few weeks after her birth, the first public photos of newborn Shiloh sold for a staggering $4.1 million in the U.S., and another $3.5 million in the U.K. In Shiloh's first official act of philanthropy, her parents donated all of the funds to African children's charities. 

Shiloh's lucrative baby photos were just the beginning of her hyper-speed rise to fame. At the tender age of eight weeks, the little one was honored with her own wax figure at Madame Tussauds in New York City. Naturally, curious fans had one burning question on their minds: Will Shiloh look more like Pitt or Jolie? They didn't have to wait long for the answer. In 2007, Jolie revealed that the bundle of joy was taking after her fair-haired papa. "She looks like Brad. It's funny because she's almost going to be the outcast in the family because she's blonde and blue-eyed," the actor told Look magazine (via The Daily Mail).

The tomboy bob

Even halfway around the world, it was impossible for the Jolie-Pitts to put distance between themselves and the paparazzi. In 2010, photographers tracked the family all the way to Budapest, where they spotted Shiloh Jolie-Pitt and her siblings at a playground. Fans marveled at how quickly the little celeb was growing. Shiloh's flaxen hair was cropped to her shoulders with a tuft of bangs that swept across her forehead. The father-daughter resemblance was uncanny. Shiloh's hair harkened back to the long, untamed locks that Brad Pitt sported back in the '90s. Taking note of the haircut, some observers were quick to label the tot's appearance as "tomboyish."

Earlier the same year, Angelina Jolie dished about Shiloh's adorable sense of style. "[She dresses] like a little dude," the actor told Vanity Fair in what appears to be a now-deleted portion of the article. "Shiloh, we feel, has Montenegro style. 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" (via Glamour).

Pitt was also happy with letting Shiloh explore her identity. In 2008, the "Ocean's Eleven" actor told Oprah Winfrey, "She only wants to be called John. John or Peter. So it's a Peter Pan thing. So we've got to call her John ... it's just that kind of stuff that's cute to parents, and it's probably really obnoxious to other people" (via People).

Super sleek

The 2014 premiere of "Unbroken" was a family affair for the Jolie-Pitts, who hit the red carpet to support Angelina Jolie's directorial work on the film. Papa Brad Pitt led the way, flanked by Shiloh Jolie-Pitt and her brothers, Maddox and Pax. The foursome were all decked out in their freshest suits and ties. Shiloh sported sleek blonde strands that were gelled back and pushed to the side. Although she was only 8 years old, the mini-icon proved that her hair game was top-tier.

As Shiloh grew older, tabloids began taking aim at her appearance. Tacky headlines sensationalized Shiloh's style by evoking outdated gender stereotypes and floating some seriously inappropriate questions about the child's identity. Some tabloids went as far as to claim that Shiloh was "blossoming into a boy." Bizarrely, one tabloid tried to stir up gender-normative drama over Shiloh's preference for playing with toy dinosaurs instead of dolls.

In an interview with Reuters, Jolie was steadfast about supporting her daughter regardless of her identity. "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. I think that is just bad parenting," stated the "Salt" actor. "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." We couldn't agree more, Angelina!

Cute and cropped

In 2015, Shiloh Jolie-Pitt joined her mother Angelina Jolie and sister Zahara at the 28th annual Kid's Choice Awards. The giddy trio was front and center to celebrate Jolie's performance in "Maleficent," for which she won Favorite Villain. Shiloh flaunted her signature style: a cute graphic tee and a comfy jacket. The little starlet also rocked a shaggy bob that was trimmed just below the nape of her neck. Shiloh's straight locks were parted to the side and pushed behind her ears to show off her blue eyes and bright smile. It was the perfect look for such a laid back, kid-centric affair. 

When the presenter announced Jolie's win, the crowd cheered wildly. Shiloh and Zahara beamed with pride as their mother accepted the coveted orange blimp. In her acceptance speech, Jolie told the audience, "I want to say that when I was little, like Maleficent, I was told that I was different. And then one day I realized something — something that I hope you all realize. Different is good. When someone tells you that you are different, smile and hold your head up and be proud" (via Today). We can't help feeling like Jolie's speech held a secret message for Shiloh. Perhaps Jolie was subtly reminding her daughter to disregard the tabloids and stay true to herself.

The skater cut

Despite her lavish life, there is one totally down-to-earth fact about Shiloh Jolie-Pitt: The girl loves her comfy clothes. Just as the mini-celeb enjoys a good pair of sweats and a bulky tee, she has also conquered the art of rocking a low-maintenance hairstyle. In 2017, Shiloh adopted a super manageable skater cut. The hairstyle featured short sides and long bangs that were styled into a golden swoop across her forehead. Complete with natural sun-drenched highlights, it was one of her most iconic looks yet.

In September of 2017, Shiloh hit the red carpet for the premiere of the film, "First They Killed My Father," which depicts the dreadful events of the Cambodian genocide that began in 1975. The premiere was a significant moment for the Jolie-Pitt family because Angelina Jolie and her son Maddox had worked on the project together. With a freshly-trimmed skater 'do, Shiloh brought her style A-game to the event. The junior celeb sparkled with pride and confidence as she sauntered down the red carpet. 

Crew cut perfection

For most people, walking the red carpet is a star-studded fantasy — but to Shiloh Jolie-Pitt, it's business as usual. The little superstar has made numerous red carpet appearances with her celebrity parents. Just like her glamorous mom, Shiloh knows how to steal the show when it comes to movie premieres and award shows. The youngster served another legendary hair moment in 2018 while attending the Annie Awards with her mother Angelina Jolie and sister Zahara. To compliment her black tuxedo and pinstripe undershirt, Shiloh opted for one of her shortest styles yet: a crew cut that featured trimmed sides with a little bit of tousled length on top.

Jolie and her brood never fail to shine at red carpet events. These outings are always a rare opportunity to observe the personalities and fashion sense of Jolie and Brad Pitt's six children. In Shiloh's case, her 2018 appearance at the Annie Awards was the latest in a string of delightfully Pitt-esque moments. Shiloh's crew cut felt like a nod to her superstar dad, who sported similar short hairstyles throughout the mid-'90 and early aughts.

Dapper like her dad

Shiloh Jolie-Pitt had another mini-Brad Pitt moment in 2019 when she rocked a medium-length cut that was parted to the side and styled with a little bit of product. This time, the youngster attended the European premiere of "Maleficent: Mistress of Evil." At the time, only three years had passed since Angelina Jolie famously filed for divorce from Pitt. Despite being separated, the exes were enmeshed in fiery legal disputes pertaining to their shared assets and custody of their children. 

"The last few years haven't been the easiest, since when I first played her. I've been through different things in my life, and I was happy to play Maleficent again. She made me feel strong again," Jolie confessed to Vanity Fair at the time. Still, the actor and her children presented a united front at the 2019 event. In a testament to their resilience, Shiloh and her siblings appeared as happy and healthy as ever.

While Jolie and Zahara opted for full glam in dazzling black dresses, Shiloh turned heads in a black jacket and crisp white shirt. The teen was noticeably taller and sporting a set of braces. Still, the mini-celeb was the spitting image of her dad. Even her body language resembled Pitt's reserved yet confident persona. Shiloh's dapper, medium-length cut had fans reminiscing on some of her father's past red carpet looks. After all, medium-length hair is a standout look for Pitt, who has rocked numerous variations of the style.

Shiloh's 'Eternals' updo

In 2021, Shiloh Jolie-Pitt took her place as a style icon when she hit the red carpet in London for the premiere of "Eternals." In an unexpected pivot, the teen queen ditched her usual tuxedo for an exquisite black and white Dior gown. Fans quickly recognized the printed dress as one that Angelina Jolie wore back in 2019. The garment's original floor-length hem was tailored to the knees on Shiloh, which gave it a fresh and more casual vibe. However, Shiloh was not finished shocking the masses with her surprise new look. In sharp contrast to her classic short styles, the young celebrity donned long blonde hair that was pulled back into a tidy bun. Days earlier at the film's Italian premiere, Shiloh rocked an elaborate updo that was parted into three sections and featured a labyrinth of French braids.

Shiloh's red carpet transformation was breathtaking, but it wasn't the first time that her grown-out locks made an appearance. In early 2021, Jolie and her kids posed for British Vogue at their home. In the photos, Shiloh could be seen rocking a sleek blonde ponytail (via People). Whether she feels like looking suave in a suit or gorgeous in a gown, Shiloh proved that she is a dynamic dresser who can pull off just about any hairstyle. And, hey — we love a girl that can do it all.

The laid-back bun

Despite inheriting a fantastic head of hair from both sides of the gene pool, Shiloh Jolie-Pitt seems content with keeping things low maintenance. As far as we can tell, this young star has no need for Brazilian blowouts or fancy hair masks — Shiloh's tried and true preference is a laid-back bun. Throughout 2021 and 2022, the junior celeb rocked this simple style in Los Angeles, London, Rome, and beyond. Most of the time, her signature blonde locks were pulled back into a slightly messy, top knot-style bun. Occasionally, Shiloh opted for a ponytail pulled halfway through for a different variation of the look. Shiloh seems to know the value of having a go-to hairstyle that's low-maintenance enough for her busy lifestyle.

Shiloh was certainly committed to the laid-back bun, but she wasn't afraid to add a little variety to her look. In May of 2022, Shiloh had a brief color moment when she experimented with red hair dye. The starlet appeared to be sporting a temporary dye that transformed her golden locks into a light brick-red color. Shiloh's style evolution continues to captivate fans — and it seems like her parents have a lot of respect for her unique and creative style. In 2020, a source told Entertainment Tonight that Brad Pitt praises Shiloh's individuality and "loves that she always stays true to herself".

The buzzcut

Long hair can be a lot to manage, especially for somebody who is used to rocking short styles — so, in early 2023, Shiloh Jolie-Pitt took the plunge and shaved her head. It was her most dramatic hair transformation yet. To the surprise of no one, Shiloh's new buzzcut looked incredibly chic on her. When she was spotted donning the new look in January 2023, Shiloh's hair clippers weren't the only thing buzzing — fans couldn't stop talking about her bold new appearance. Whether you love or hate the feminine buzz cut, the historical and social contexts of this hairstyle are worth acknowledging. Many women have embraced the buzz cut as a way to challenge and redefine conventional beauty standards, which are often narrow, exclusionary, and heteronormative.

Shiloh joins an elite roster of famous women who have shaved their heads, including Grace Jones, Kate Hudson, Natalie Portman, Doja Cat, and many more. But we imagine that, for Shiloh, the most important member of the feminine buzz cut club is her own mother, Angelina Jolie. Shiloh's radical haircut has us daydreaming about 1998, when Jolie sported her own version of the fierce buzz cut. As you might have guessed, Shiloh's ever-supportive mom was all about the teen's new 'do. In February of 2023, Jolie treated fans to an up-close photo of the buzz cut via her Instagram. The image was artistically cropped in half and featured the back of Shiloh's freshly-buzzed head.