Shiloh Jolie's Ever Changing Look Throughout the Years: From Tomboy to Teenage Icon

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Shiloh Jolie effortlessly embodies the best of Angelina Jolie and Brad Pitt. Despite growing up in the public eye, she's boldly forging her own path. People have seen her undergo body and style transformations, and yeah, some have criticized her.

But now, she's confidently embracing her true self. Lately, Shiloh even made some major decisions on her terms.

She's the first biological child of Hollywood's biggest at-the-time power couple.


When Angelina Jolie and Brad Pitt welcomed their daughter, originally known as Shiloh Jolie-Pitt, in Swakopmund, Namibia, it sparked a lot of excitement among fans, and the media covered the story from every angle. Shiloh, born May 27, 2006, joined her siblings Maddox, Pax, and Zahara. Even though she had older siblings, Shiloh was the first biological child of Angelina and Brad, who were both there for her birth.

Even from birth, Shiloh had her dad's eye color but her mom's pouty lips. Two years later, Shiloh welcomed her younger siblings, Knox and Vivienne, into the family. They were also born via C-section, just like Shiloh.

Initially, Jolie was nervous about becoming a mother. She confessed that she never thought she could be a mom due to her unstable youth. However, she eventually decided to embrace motherhood and found it surprisingly easy to love and dedicate herself to her children. The real challenge, she wrote, was realizing that she was now responsible for ensuring everything was okay from then on.

Shiloh has always been in the media spotlight since birth.

In the years since Shiloh Jolie was born, people couldn't help but wonder if she'd take after Angelina Jolie or Brad Pitt more. With her naturally light blond hair, some thought she got it from her dad, while others saw similarities to young Angelina—who, fun fact, was also a natural blond as a kid.

Being the first biological child of Hollywood's power duo, meant Shiloh grew up under the paparazzi's constant flash. Every move she made became global gossip. From her cute baby days to her current stylish teenage years, she's always reflected the star power of her folks.

As she's grown up, Shiloh's developed her own sense of style and identity. From rocking a cool tomboy look with a bob to embracing bold hair changes as a confident teen, she's definitely evolved.

Shiloh's early desire to live as a boy unearthed.


When Brad Pitt revealed on Oprah that his then-almost-two-year-old daughter, Shiloh Jolie-Pitt, preferred a "male" name and expressed a desire to dress and identify as a boy, tabloids took notice. Angelina Jolie later elaborated, saying, "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."

The family's response was nonchalant, and the media followed suit. While Shiloh's transition drew interest in celebrity circles, it wasn't sensationalized, and the press refrained from labeling Brangelina as the parents of a transgender child.


Shiloh had the freedom to express herself. From 2007 to 2009, she rocked a cute bob haircut that suited her well and showed off her beautiful blond hair. Angelina Jolie praised Shiloh's lively personality in an interview, though she joked about recognizing a mischievous side, saying she might take after her. Despite any speculation, her parents fully embraced Shiloh's individuality.

Brad Pitt shared in an interview with Oprah Winfrey that Shiloh once preferred to be called "John" or "Peter," which he described as a "Peter Pan thing." Besides her name, Shiloh also enjoyed dressing like a boy. Angelina respected her daughter's choices, saying she found them fascinating, but she never pressured Shiloh to be anyone other than herself, believing that would be "bad parenting."

Her fashion revolution

Shiloh made a striking debut with a new look at the 2021 Eternals premiere in Los Angeles. She dazzled on the red carpet in a black and white tank dress and ballet shoes, a bold departure from the slacks she usually wore at such events.

Continuing to redefine her style, Shiloh also discovered a passion for dancing, an interest not shared by her parents. In 2022, a video of her showcasing her impressive dance moves to Doja Cat's "Vegas" at the Millennium Dance Complex went viral on YouTube, racking up millions of views.

Despite her acclaim on the dance floor, Shiloh faces scrutiny in other aspects of her life. As 2023 began, she drew media attention with a new buzz cut, reminiscent of her father's hairstyle, a dramatic shift from her formerly long blonde locks.

Sadly, her new look faced criticism on social media. Some readers shared their opinions about Shiloh in the comments section. One person remarked, "She really looked so much better before." Another wrote, "She looked so beautiful when she embraced her feminine side." Someone else commented, "Thought she liked being a girly girl," while another simply stated, "Looks like Brad."

Shiloh has undergone major transformations and decisions in her life, including her recent choice to drop her father’s last name.

Preview photo credit TIZIANA FABI/AFP/East News, Mirrored / Youtube


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