Angelina told Vanity Fair in a 2010 interview that Shiloh has been exploring gender since age three. “She wants to be a boy,” Jolie said. “So we had to cut her hair. She likes to wear boy clothes. She thinks she’s one of her brothers.”

Over the years, Shiloh was always encouraged by her parents to dress the way she wanted. As a child, she would don casual separates – polo shirts, jackets, blazers, shorts, dark trousers, jeans and oversized tracksuits.

Another year, another surgery

“I have spent the last two months in and out of surgeries with my eldest daughter, and days ago watched her younger sister go under the knife for a hip surgery,” she wrote.

Entertainment Tonight later disclosed that it was Zahara and Shiloh who underwent surgery, and Shiloh was spotted on crutches soon afterwards in March 2020.

But it seems Shiloh’s medical dramas are far from over, because the teen was photographed on crutches again earlier this year in April 2021, prompting speculation of yet another surgery. Fans were left concerned about photos of Shiloh using the crutches on the tarmac to catch a private flight along with sister Zahara.

Since then, Shiloh has been photographed multiple times back on her feet, so here’s hoping she’s fit and healthy again.

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Shiloh’s sisterly bond with Zahara

But after both undergoing surgery together, it has brought the siblings even closer together. “I saw how all my girls so easily stopped everything and put each other first, and felt the joy of being of service to those they love,” Jolie said her Time essay.

Shiloh and Zahara may have wisely stayed indoors throughout the pandemic, but when they have stepped out, it’s been closely together, including multiple shopping trips with their famous mum.

Brad is still fighting for custody of Shiloh and her siblings

Angelina and Brad announced their separation in 2016 and were declared legally divorced in 2019, but their custody arrangements are still raging on years later.

Brad is reportedly seeking 50/50 custody of Shiloh and her five siblings: Maddox (19), Pax (17), Zahara (16), Shiloh (14) and twins Vivienne and Knox (12). However, Angelina is apparently fighting it tooth and nail, and might even bring the kids into it.

While there is a separate filing concerning testimony from the former couple’s youngest children, both Brad and Ange need to grant permission from the court to involve minors Shiloh, Knox and Vivienne in their divorce proceedings.

According to court records, Angelina has filed various documents making it clear that she is willing to offer “proof and authority in support” of alleged domestic violence during her divorce trial.

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Dancing her way into show business?

If new photos of her are anything to go by, Shiloh has shot up in the height department during her teenage years. And it seems she might be putting those new long legs to use.

A month after showing off her new look in January, Shiloh was spotted inside a Los Angeles dance studio in Pasadena, California, on February 23.

It’s unclear if she was leaving a dance practice or just visiting the studio, but the famous teen looked stylish as usual in ripped black jeans and a matching hoodie.