These Photos Show How Shiloh Jolie-Pitt Is Growing Up To Be A Real Style Chameleon

In the stinging aftermath of the Brangelina breakup, there’s one thing we can take solace in: they raised some pretty great kids. And their first biological child together, ten-year-old Shiloh Nouvel Jolie-Pitt, is perhaps the most famous of them all. What’s more, Shiloh is seeming to not only be dealing with her unusual upbringing very well, but also slowly evolving into a style trendsetter for the kids of today.

Shiloh was born in May 2006, and – seeing as how she’s the daughter of Angelina Jolie and Brad Pitt, two of the best-looking people in the entire world – there was no chance that she wouldn’t be a cute baby. And whenever she was out with her famous parents, she was always dressed in cute baby clothes, too.

Plus, the media and general public were always very interested in what baby Shiloh was wearing. In fact, whenever she was photographed wearing something, there was often a sudden rush of parents desperate to buy it for their own children.

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As Shiloh grew bigger and moved with her family to a gorgeous New Orleans villa, she became even more adorable. And she always looked nice, too; she never seemed to be photographed wearing torn or messy clothes, like you’d expect from the average two-year-old. Celebrity kids just seem to have a layer of gloss that the rest of us lack…

In 2008 she even made the much-reviled footwear brand Crocs look good. Many people would wince at the idea of bright green Kids Crocs Caymans, but Shiloh – possibly with help from her parents – made them work.

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Before long, Shiloh had reached the age where kids normally get to pick their own clothes. And although like her siblings she picked fairly neutral-looking threads, she looked lovely and much like the quintessential “girly girl.”

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In fact, she seemed to have inherited her mother’s timeless sense of fashion. And although her facial features and blonde locks were more reminiscent of her father, in poise and in style she looked a lot more like Jolie.

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But this all changed. Come 2010 Shiloh’s hair was cut into a cute boyish ’do, and she was wearing decidedly more tomboyish clothes. “She wants to be a boy,” Jolie told Vanity Fair that year. “So we had to cut her hair. She likes to wear boys’ everything. She thinks she’s one of the brothers.”

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The media was rather surprised at this turn of events. “Do Brad and Angelina Want To Turn Shiloh Into A Boy?” one headline speculated. But it seemed that the Jolie-Pitts were simply very liberal parents who encouraged their children’s self-expression.

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And when Shiloh dressed how she wanted, the results were pretty spectacular. For example, People magazine dubbed the $425 Nutcracker-inspired red jacket she wore in December 2010 a “mini must-have.”

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And Shiloh also seemed to like casual-but-cool T-shirts that showed off her likes and personality. The media labeled her style as “fearless,” and it really seemed to be. Plus, it was clear that she had her parents’ support.

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“I would never be the kind of parent to force somebody to be something they are not,” Jolie told Reuters in 2010. “I think that is just bad parenting. 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.”

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However, people were starting to wonder: while Shiloh’s androgynous style looked great, was it more than merely a fashion choice? Did she enjoy dressing like a boy, or was she actually a boy? Was she transgender?

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Rumors continued to spread over the media and over the blogosphere as Shiloh continued to wear suits while her sisters wore dresses. At her parents’ wedding in 2014, for example, she wore a cute little suit-shorts combo and appeared to be very comfortable in it.

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Soon enough, gender specialists were called upon by the media to analyze the Jolie-Pitt family. And the consensus seemed to be that, while it was possible that Shiloh was transgender, as long as she was suffering no distress it was best to let her dress how she wanted and see what choices she made. Which was exactly what her parents seemed to be doing already.

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However, Jolie continued to refer to Shiloh as her daughter, indicating that whatever decision Shiloh might make about her gender identity, it hadn’t been made yet. And Shiloh continued to dress like a boy, and boys’ hats and T-shirts combined with her smile looked adorable.

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At the 2014 premiere of her mother’s movie Unbroken, meanwhile, she wore a suit just like her brothers and looked effortlessly cool and androgynous. She also looked very confident, which is of course the ultimate key to any and all fashion choices.

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And throughout 2015 Shiloh continued to wear boyish clothes while rocking an androgynous hairstyle, too. She looked like quite the little starlet when she attended the Nickelodeon Kids’ Choice Awards with her mother and sister that year, for example – even though her clothes were very casual.

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And when she did a Vogue photo shoot with her famous family, she dug out a quite incredible Mad Hatter-style hat, as well as the red jacket she’d worn as a younger child. In fact, it looked as if she’d just run right out of a storybook.

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Shiloh’s last major public appearance was at the premiere of her mother’s movie Kung Fu Panda 3 in January 2016, where she wore a simple but sophisticated vest and T-shirt combo. It’s clear that no matter what she decides to do with her later life – or if she’ll even still be called “she” then – she’s certain to rock it.

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