Shiloh Jolie-Pitt's Remarkable Hairstyles Over The Years

By eschewing pigtails and long hairstyles for years, Shiloh Jolie-Pitt defied many people's expectations of how a little girl should look. Her follicular non-conformity has also helped fuel the public's fascination with her, as if being the offspring of Angelina Jolie and Brad Pitt isn't enough to make her a top target of the tabloids and the paparazzi.

As of this writing, she hasn't given any in-depth interviews about her life, so some people have built a narrative around Shiloh using quotes from her parents and images of her from babyhood to adolescence. Much of the speculation about Shiloh's psyche has been based on how she wears her hair and the clothing she chooses to wear. Her parents allow her the freedom to make these decisions, which is something Jolie has been forced to defend on occasion. "I let her be who she is," the mother of six told Stylist (via the Mirror) in 2010. "People look at kids and think they should wear certain types of clothes. I think children should wear what they want and express themselves." This belief also applies to hair.

Shiloh's much-buzzed-about decision to wear her hair cropped short hasn't just made her stand out from other girls her age over the years; Jolie revealed that her daughter's blonde locks made her the odd one out in her own family long before she was able to voice her hairstyle desires.

Shiloh Jolie-Pitt was a four-million-dollar baby when she was introduced to the world on the June 2006 cover of People. According to Forbes, Angelina Jolie and Brad Pitt got their infant daughter involved in philanthropy early by donating the hefty payment for her baby pics to nonprofits benefiting children in Africa. 

Shiloh didn't have much hair to speak of when she became a peacefully napping cover girl, but after 20 months of growth, Jolie told Look magazine (via the Daily Mail) that the little girl was starting to resemble her dad. However, Jolie added, "It's funny because she's almost going to be the outcast in the family because she's blonde and blue-eyed." While Shiloh shares her genetics with her mom and dad, she was joining an international family; her older brothers, Maddox and Pax Jolie-Pitt, were adopted from Cambodia and Vietnam, respectively, and her older sister, Zahara Jolie-Pitt, was adopted from Ethiopia. They all have dark hair and dark eyes. 

Inheriting her father's flaxen hair color made Shiloh an excellent casting choice for the role of his character's daughter in the 2008 movie "The Curious Case of Benjamin Button." There was nothing remarkable about her tresses at that time, but she seemed destined to do some edgy hairstyle experimentation someday; her mother, after all, did tell InStyle that she bleached her hair and colored it with a Sharpie during her punk phase.

In 2009, Shiloh Jolie-Pitt was photographed looking like a little rockstar during a visit to a Washington, D.C. toy store. Her hair was styled in a long bob, and by accessorizing with a pair of sunglasses with bright blue frames, she was, surprisingly enough, channeling late Nirvana frontman Kurt Cobain. The dark hoodie pulled up over the cherub-cheeked toddler's head upped her cool factor even further.

Shiloh was rocking her stylish lob when she visited her mom at a hospital in Nice, France in 2008. At the time, Angelina Jolie was pregnant with twins Vivienne Marcheline and Knox León Jolie-Pitt. Brad Pitt was photographed carrying Shiloh, who was wearing a pristine white pinafore that was so not rock 'n' roll. 

Not long after the twins were born, Pitt appeared on "The Oprah Winfrey Show" and made some remarks about Shiloh that would be regurgitated in rumors and speculative tabloid pieces about the little girl for years to come. It turns out that the tot wasn't at home listening to the "Nevermind" album but dreaming of visiting Neverland. "She only wants to be called John. John or Peter. So it's a Peter Pan thing," Pitt said (via People). "So we've got to call her John. 'Shi, do you want ...' — 'John. I'm John.' And then I'll say, 'John, would you like some orange juice?' And she goes, 'No!'"

In 2008, Suri Cruise, the daughter of Tom Cruise and Katie Holmes, topped Forbes' list of Hollywood's biggest baby influencers. Shiloh Jolie-Pitt finished in second place but soon made a move that would put Suri's nepo baby supremacy in jeopardy: She cut her hair short. In 2010, Angelina Jolie spoke to Stylist (via the Mirror) about her daughter's hairstyle decision. "Shiloh cried and said: 'Please cut my hair off, I don't want to have long hair,'" the actor recalled. "I'm not going to leave it long because somebody thinks I should." That same year, Jolie told Vanity Fair that Shiloh had adopted what she described as "Montenegro style." Said the mom, "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."

Soon, Jolie was being mom-shamed for allowing Shiloh to have short hair and wear clothing that some people viewed as boyish. A cover of Life & Style blared, "Why Is Angelina Turning Shiloh Into a Boy?" The magazine enlisted Glenn Stanton, a member of the conservative Christian ministry Focus on the Family, to help it scold Jolie. Stanton's organization is known for its support of anti-LGBTQ+ policies, and he suggested that Jolie should have been forcing her daughter to adhere to a conservative gender stereotype. "It's important to teach our children that gender distinction is very healthy," he claimed (via Advocate). 

But Shiloh said: Short hair, don't care. And honestly, good for her!

The haircut pearl-clutchers and gender conspiracy theorists got a break from being outraged in 2011 when Shiloh Jolie-Pitt grew her hair out into a bob. But ever the rebel, she channeled her mom by rocking a tattoo — albeit one of the temporary variety – on her right leg during a visit to a Benihana restaurant in London. 

Shiloh was sporting her new chin-length hairstyle when she was photographed having a playdate with Kingston Rossdale, the son of No Doubt frontwoman Gwen Stefani and Bush lead singer Gavin Rossdale. InTouch (via Yahoo! Entertainment) even claimed that Shiloh was harboring a little crush on her fellow nepo baby. (There's no word on whether she tried to impress him with her wash-off ink.)

Lest you think that the new length of Shiloh's golden mane was something imposed on her by her parents, Angelina Jolie insisted that she just wants her daughter to be true to herself always. She also had a message for everyone who was making assumptions about Shiloh based on her appearance. "I don't think it's for the world to interpret anything," Jolie told the Daily Mail in December 2010. "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."

In 2014, Shiloh Jolie-Pitt got her hair cut short again, this time opting for a pixie cut with long bangs. (It was like Kate Gosselin's famous hairdo but way cooler.) The move came two years after Life & Style claimed that Brad Pitt was concerned about his daughter being bullied over her cropped 'do. "This is a culture where kids get picked on if they don't look like other kids," a psychotherapist warned the mag. But again, Shiloh seemed to have zero interest in following the crowd. Her haircut was also a practical style for a rebellious sk8r grrl like herself — Angelina Jolie told E! News that Shiloh had become so fond of skateboarding that the activity was incorporated into her 8th birthday party that year.

While Shiloh's pixie haircut was clearly cool with Angelina, one source claimed the actor did not want her daughter dressing like a pixie. "[Brad Pitt's mother] Jane still insists on buying her fairy costumes and princess dresses, which Angelina finds very disrespectful," the insider told The Standard. There was also no way Shiloh was going to put on a long, princess-y wig to play the role of young Sleeping Beauty in her mom's 2014 Disney movie "Maleficent." Jolie recalled to Elle, "I asked Shiloh about being Aurora, and she laughed in my face. She said she'd be a horned creature." How punk rock is that?

For the December 2014 premiere of her mom's movie "Unbroken," Shiloh Jolie-Pitt wore her hair slicked down. It was the perfect hairstyle to complement the dapper suit that she rocked on the red carpet. Angelina Jolie had to miss the event because she had chickenpox, so Brad Pitt showed up in her stead. Seeing Brad and Shiloh side-by-side didn't have Elle remarking on their family resemblance; instead, Shiloh's gelled tresses had the magazine comparing her appearance to that of "Boardwalk Empire" star Michael Pitt (no relation).

Model Amber Rose also decided to comment on Shiloh after seeing photos from the event. She shared one of them on Instagram and included the caption, "How gorgeous is John Jolie Pitt?! Born into the perfect family for him. #TransKids #LoveurKidsNoMatterWhat #Support." Rose later deleted the post, possibly because she learned that Shiloh's parents have never said that she's transgender. Jolie indicated that the "John" phase was over while speaking to the Daily Mail years prior and also used female pronouns when referring to her daughter, so Rose probably should have taken her cues from Shiloh's mom before remarking on the child. 

As Jolie eloquently said to Reuters, "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. ... Society always has something to learn when it comes to the way we judge each other, label each other."

One commonality between most of Shiloh Jolie-Pitt's hairstyles is the presence of a deep side part. It was there when she attended the 2015 Kids' Choice Awards, for which Shiloh decided to keep her overall look casual. Her hair had grown out just long enough that she was able to push it behind her ears, and she wore a gray hoodie over a funky black t-shirt emblazoned with an image of a giraffe wearing sunglasses.

The tabloids kept conjecturing that Shiloh was identifying as a boy; one example was a 2015 Radar report claiming that she had "gender identity issues." Having the media constantly speculate about your gender identity based on your hairstyle, clothing choices, and something your parents once said about you when you were a very young child seems like it would be rather frustrating, but Shiloh kept on defying her critics by refusing to conform to their favored female gender stereotypes. Daring to be different was actually something Jolie touched on during her acceptance speech for the best villain award at the Kids' Choice Awards. 

"When I was little, like Maleficent, I was told that I was different, and I felt out of place — too loud, too full of fire, never good at sitting still, never good at fitting in," Jolie said, per Glamour. "Then one day I realized something, something that I hope you all realize: Different is good."

We were starting to get the feeling that Shiloh Jolie-Pitt enjoys red-carpet events when the then-11-year-old showed up to support her mom at the 2017 Toronto International Film Festival. She and Angelina Jolie were joined by the rest of the Brangelina brood — sans Brad Pitt. By then, he and Jolie had announced that they were getting divorced. The two films Jolie was in Toronto to promote were "First They Killed My Father" and "The Breadwinner," an animated movie about an Afghan girl living under Taliban rule. To help her family survive, she decides to disguise herself as a boy.

Shiloh had gone for another big chop ahead of the event, readopting the layered pixie cut with a dramatic side swoop. The ends appeared razor cut, and the style was fairly similar to Jennifer Lawrence's famous pixie cut. Shiloh's tresses were tousled, giving her a carefree vibe. While she was proving to be one photogenic kid, one source claimed that she was more intent on getting behind the camera at that time. "Shiloh is very interested in photography," a source told Us Weekly in December 2016, after Jolie was spotted buying her daughter a vintage camera. 

That January, Jolie had told "Today" that she didn't really want her kids to follow in their parents' footsteps. "We've always said, if they're gonna be actors, I hope they do something and then be actors," she said.

Before she attended the Annie Awards in 2018, Shiloh Jolie-Pitt lost the length around her face. This transformed her hairstyle into a crew cut. She sported a snazzy suit — sans tie — on the red carpet, which she walked with Angelina Jolie and Zahara Jolie-Pitt. The trio was there to see if "The Breadwinner" would win any awards, and it did; it was named the best independent animated feature.

When Jolie isn't busy producing award-winning animated films and other projects, she spends some of her free time helping her kids maintain their manes. "I often cut the kids' hair. They ask and I love that," she told Hello! that same year. With all the traveling she and her children do, knowing her away around a pair of shears must come in handy; when you're a member of one of the most famous families in the world, it's probably a pretty big hassle to book a hair appointment somewhere you aren't familiar with. 

An example of one trip Shiloh accompanied her mom on in 2018 was when they visited Syrian refugees in Jordan. They were joined by Zahara, and People reported that Jolie's daughters requested to go on the UNHCR trip.

For the 2019 European premiere of "Maleficent: Mistress of Evil," Shiloh Jolie-Pitt decided to slick down her hair with a little gel. Hola! observed that the hairstyle made her resemblance to Brad Pitt even more striking than usual because it was so similar to how her dad has styled his own hair in the past. Shiloh attended the event with Angelina Jolie and Zahara Jolie-Pitt, and the trio coordinated their looks by wearing black ensembles. Shiloh opted for a pair of slacks, a bomber jacket with gold stripes, and Converse sneakers.

Jolie told People that she offered Shiloh and her siblings the opportunity to appear in the "Maleficent" sequel but got turned down. "None of my kids want to be actors," she said. "[They're into] business, humanitarian affairs, things like that." While Shiloh once again didn't want to play a fairytale character alongside her mom, this wasn't a sign that she didn't want to spend time with Jolie at all. 

Shiloh turned 13 in May 2019, and ET reported that her mother treated her to a fun-filled birthday party at The Basement LA, a venue that offers escape room experiences. That same year, Shiloh was spotted hanging out with another young celeb known for rocking short hair, "Stranger Things" star Millie Bobby Brown. There's no word on whether Brown attended her pal's birthday bash.

Shiloh Jolie-Pitt was 15 years old when she rocked her first updo on the red carpet. For the 2021 premiere of her mom's Marvel movie "The Eternals," she wore her dark blonde hair clipped back, leaving two delicate tendrils hanging down. Shiloh had on white ballet flats and a tan dress with an asymmetrical skirt, which turned out to be borrowed from her mom; according to ET, it's what Jolie wore while giving a group of beekeepers their diplomas at the French Apidology Observatory. Zahara Jolie-Pitt, meanwhile, borrowed one of her mom's Oscar dresses. "We did all vintage and upcycled my old stuff," Jolie told ET. Browsing through Jolie's closet has to be a wonderful way to learn about making sustainable fashion choices.

Unfortunately, some people had to be all weird about Shiloh Jolie-Pitt wearing a dress and having long hair; a Daily Wire piece about her new look bore the controversial title, "Tomboy Goes Glam: How Shiloh Jolie-Pitt Escaped The Trans Craze To Become A Lovely Young Lady." But while Shiloh had started to adopt a more traditionally feminine red-carpet look by borrowing her mom's clothes, this doesn't mean that Jolie wanted her to fit a certain mold. "I'm that mom that if I see your rebellious spirit, it warms me," Jolie told People (via Today). "And I think, 'Good for you, you got fire.'"

It soon became evident that Shiloh Jolie-Pitt has a preference when it comes to how she wears her hair when it's long: She keeps it off her shoulders. She wore another updo to the Rome premiere of "The Eternals." This time, she decided to get a bit more adventurous by including French braids on the sides. The rest of her hair was twisted up into an elegant top knot. She made the smart sartorial decision to keep her outfit simple, so her intricate hairstyle wasn't competing with it. However, her little black dress with a flared skirt and front tie was still sophisticated and fun.

Shiloh wore her hair pulled up in another top knot for the UK premiere of "The Eternals," where she rocked a black-and-white patterned Dior dress that her mom loaned to her. Of Shiloh's slew of red-carpet appearances, a source told InTouch, "Angie's making sure Shiloh doesn't think of it as validation because it's all about appearances. Angie has instilled in all her kids that what counts is on the inside, but that her business, unfortunately, puts a lot of focus on what's on the outside."

The paparazzi also started regularly photographing Shiloh with her hair pulled up in a messy top knot, and she was even pictured rocking the hairstyle in a 2022 picture on Jolie's Instagram page. It was taken during a trip to Cambodia to do conservation work for the Maddox Jolie-Pitt Foundation.

In early 2023, dancing queen Shiloh Jolie-Pitt decided that she was done pulling her hair back before hitting the dance floor — she debuted a new buzzcut hairstyle. It was reminiscent of the shorn look that Angelina Jolie rocked way back in 1997. Jolie was filming "Gia" at the time, and the role required her to lose her long, dark locks. According to Variety, she had to wear wigs throughout filming and even had one glued to her scalp for a motorcycle scene.

Angelina shared a photo of the back of Shiloh's buzzed head on Instagram in February 2023. She revealed that she and her daughters had sent locks of their hair to artist Prune Nourry, who was creating an exhibition to raise awareness on the subjugation of Iranian women.

Shiloh decided to give her buzzcut a funky update that August by dyeing it pink, and we're guessing that Jolie was supportive of the then-17-year-old's bold new look. But while Shiloh might enjoy channeling her mom's edgy '90s style, Jolie insists that none of her kids are exactly like her. "Having children saved me — and taught me to be in this world differently," she told Vogue in September 2023. "I think, recently, I would've gone under in a much darker way had I not wanted to live for them. They're better than me, because you want your children to be."