n recent years Brad Pitt and Angelina Jolie’s biological daughter Shiloh has charmed the public with her transformation from a tomboy to an elegant lady.

In 2023, 16-year-old Shiloh shocked the public by cutting her hair and wearing boyish clothing and shoes again.

Her mother, Angelina, said Shiloh was a family outcast after birth, but her father, Brad encourages her to be whoever she wants.

Angelina Jolie and her ex-husband, Brad Pitt, share six children, including Shiloh Jolie-Pitt and her sister Zahara Jolie-Pitt. A few years after the COVID-19 pandemic began, Shiloh shocked the public by dressing more femininely.

The teenager was seen in gowns, heels, and makeup, which surprised viewers as she was known to dress more tomboyish. In 2021, Shiloh and Zahara enjoyed the “Eternals” press tour.

The siblings tagged along to the events with their famous mother and got to travel the world. The sisters got to be at press events ahead of the film’s premiere and even joined Angelina on the red carpet several times.

During the UK premiere of the “Eternals,” Shiloh rewore a dress that her mother was seen wearing in 2019. The young girl looked like her mother while dressed in the Dior gown, which she altered to suit her.

It was the second time that Shiloh changed one of Angelina’s dresses to attend an “Eternals” red carpet event. A week before, she was at the Los Angeles premiere with a dress her mother had worn at the “Women for Bees” event in July 2021.

The gown Shiloh wore was a deconstructed version of a Gabriela Hearst dress. However, in early January 2023, Angelina’s daughter appeared to have returned to her boyish dressing style.

The then 16-year-old girl shocked fans by appearing in a black hoodie, matching sneakers, gray shorts, no makeup, and a buzz cut. Shiloh was spotted shopping with her older sister, Zahara, then 18.

The siblings looked happy as they walked by flashing cameras. Before getting a buzz cut, Shiloh had longer blonde hair, and her style evolution has made headlines over the years.

It’s no surprise that Shiloh has had so many tongues wagging through the years because she’s always stood out, even when younger. Her mother once unusually categorized her differentness.

Mom Angelina Called Tomboy Daughter “Outcast”
When Shiloh was 20 months old, Angelina said her biological child was “going to be the outcast” in her ethnically diverse family. Amongst her three other adopted siblings in 2007, Shiloh was the only one with blue eyes and blonde hair.

At the time, Angelina and Brad were also parents to Maddox from Cambodia, Pax Thien from Vietnam, and Zahara from Ethiopia. The “Salt” actress also noted how Shiloh resembled her father and set her even more apart from her siblings.

The “Beowulf” star explained how she wouldn’t have minded not having biological children but changed her mind after seeing Brad with Maddox and Zahara after bringing the latter to the US. The actress realized how much he loved them and that a biological child wouldn’t be a threat.

Angelina also had a deep connection to her adopted children due to their childhood pain. The “Maleficent: Mistress of Evil” star described Zahara, Maddox, and Pax as “survivors” and how she “felt so much more” for the trio, stating:

“Shiloh seemed so privileged from the moment she was born.”

In 2011, Angelina revealed how Shiloh, then five, loved having temporary tattoos and wearing pirate outfits. According to a source, the actress’ daughter even picked out a clown costume while at Los Angeles’ Ozzie Dots.

The insider hilariously shared that Shiloh allegedly wanted to wear the costume at the store, but Angelina said “no.” When the actress’ daughter was two-and-half years old, she only responded to the name “John.”

Brad said his daughter only wanted to be called “John” or “Peter,” and the latter was because of a Peter Pan phase. When he used her nickname “Shi,” the little girl would say she was “John” and only responded to the name, with her father adding:

“It’s just that kind of stuff that’s cute to parents, and it’s probably really obnoxious to other people.”

In 2010, Shiloh’s tomboy phase was alive and well, with her preferring to wear clothes designed for boys. She wore tracksuits, ties, slacks, suits, and jackets as she liked dressing like a boy.

In 2022, it was revealed that Shiloh [Jolie-Pitt] had gotten into dancing and was great at it!

Angelina said that her daughter wanted to be a boy at the time, and they had to cut her hair. The actress speculated that Shiloh thought she was one of her brothers, but no matter how she presented herself, her parents were proud of her.

Dad Brad Is Proud of Daughter Who Always Stays True to Herself
In May 2020, Shiloh turned 14, and a source claimed her father was “proud” of who she had become. Brad allegedly loved that his daughter always stayed true to herself and was good to her sisters and brothers.

Although Brad didn’t attend the “Eternals” press tour in 2021, an insider said the parent supported his children and whatever made them happy. The Jolie-Pitt children were old enough to make their own decisions, and their father didn’t stop them.

The source claimed the actor encouraged his six children to “be whoever they want to be” and wouldn’t have asked for anything different. The siblings enjoyed being on the red carpet with their mother, but they were allegedly more casual with their father at home.

The insider said Brad spent time out of the spotlight with his children at home. When the children were with their famous father, they were reportedly “homebodies” with good routines.

In 2022, it was revealed that Shiloh had gotten into dancing and was great at it! After a video of her dancing with her dance group went viral, Brad said her performance “brings a tear to the eye” and that his daughter was “very beautiful.”

The “Bullet Train” star also opened up about all his children. Brad reiterated that he loved it when they found their way, found things they were interested in, and flourished.