Shiloh Jolie, 19, Has Totally Transformed Since Leaving Angelina's Nest

Shiloh Jolie is all grown up, and it happened right before our very eyes. And, like her fellow celeb kid, Suri Cruise, who's transformed greatly since jetting off to college, 19-year-old Shiloh has changed a great deal since leaving her mother, Angelina Jolie's nest.

Shiloh was born while Angelina and her then-husband, Brad Pitt, were on vacation in Namibia in the summer of 2006. Since then, she has become one of the most visible Jolie-Pitt kids, though she infamously dropped the Pitt from her name amid her parents' contentious divorce. And yet, she's still managed to live a much less public life compared to other nepo babies. "None of my children want to be in front of the camera [at] this time..." Jolie shared with "Good Morning America" in November 2024 (via People). "Shiloh's extremely private," she continued, adding, "They weren't born with privacy, right? So, I hope that they can have that as they grow old. So we'll see."

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Despite Shiloh's aversion to celebrity life, she's been photographed out with her famous family over the years, and has gone through a few distinct phases. When she was four years old, Angelina revealed that Shiloh wanted to be a boy who fit in with her brothers and dressed her as such during a profile with Vanity Fair (via Today). However, her teen years brought about a more feminine era for the young girl, and there were occasions on which she wore more feminine ensembles to red carpet events. Her style has evolved again since then, of course, with Shiloh embracing a more casual, sporty appearance since leaving home.

While most offspring of the super rich and famous yearn to stand out against their parents' fame, Shiloh Jolie seems content to blend in with the crowd and march to the beat of her own drum. The famous kid, who has a nearly non-existent social media presence, seems wholly uninterested in being flashy and flamboyant or bringing too much attention to herself, at least if her clothes are any indication. As you can see above, most days, Shiloh chooses to wear comfortable clothing, consisting of oversized t-shirts, sweatpants, and hoodies. She's also kept her blonde hair cut short, cropped with fringe bangs or pulled into a messy bun.

However, Shiloh's fashion isn't the only thing that's continued to change over the years. She's also taken another important step towards establishing independence. Although she could probably stay forever, she's moved out of her mother's home. According to the Daily Mail, Shiloh moved into a Los Angeles condo with her rumored girlfriend, Keoni Rose, over the summer of 2025. The outlet published photos of the pair hanging out outside of the property before Shiloh sent Rose off with a warm hug. However, the publication noted the move-in was temporary, which was likely a great relief for her mom, Angelina Jolie. "There is no way Angie is calm about this — she likes all her birds in one nest," revealed a source, adding, "'But she has peace of mind because security goes wherever her kids go. Mama bear makes sure her cubs are watched over by ex-Navy SEAL security personnel."