The teenager's signature baggy clothes had been replaced with cute cut-off jean shorts and a fitted hoodie, and her formerly close-cropped locks were swept up into a sleek bun.
Noted an onlooker, "The spiked hair and boys' clothing were gone." Her transformation from tomboy to teen beauty queen isn't the only big change for Shiloh, who turned 15 on May 27.
"She's really come out of her shell these last couple of years," says an OK! insider of Jolie and ex-husband Brad Pitt's first biological child. (The former couple also share Maddox, 19, Pax, 17, Zahara, 16, and 12-year-old twins Knox and Vivienne.)
"Shiloh blows people away with how smart she is. She knows a ton about art and architecture from her dad and is versed in humanitarian issues thanks to her mom." But she's also very much her own person, adds the insider: "There's a maturity to her that just draws people in."
Shiloh's been in the public eye since before she was born. "She grew up in the spotlight," says the insider, "and somehow managed to cope with all the attention she's gotten through the years."
She famously told her parents she wanted to be called "John" instead of Shiloh when she was just a toddler. "She wants to be a boy," Jolie said in 2010. "So we had to cut her hair. She thinks she's one of her brothers."
Shiloh was a fearless kid — and determined to keep up with Maddox and Pax. "It might seem random to some people, but she had two rambunctious brothers and wanted to emulate them," the insider says of Shiloh's decision to go by John.
"But as she got older, she could beat them at soccer, shooting hoops, you name it. She no longer needs a boy's name to hold her own!"
She's mellowed out in recent years, adds the insider. Jolie gushed about her girl's tender side in a March 2020 essay discussing how Shiloh and sister Zahara fared after both underwent surgery.
"I have watched my daughters care for one another. My youngest daughter studied the nurses with her sister and then assisted the next time."
The insider says Shiloh looks after her younger siblings, especially since Pitt and Jolie called it quits in 2016. "She's turned into a very caring, sensitive and nurturing soul."
Pitt and Jolie's divorce hasn't been easy on Shiloh. The insider says she does her best to remain neutral.
"Maddox has clearly sided with Angelina, but Shiloh just wants her family to be whole and happy again. She loves both her parents, and while she understands things will always be different, her dream is to see them become friends."
She was hoping for a peaceful reunion between the Those Who Wish Me Dead star, 46, and 57-year-old Ad Astra actor at her 15th birthday party.
Despite the update in the custody case, the insider says the stars still made sure Shiloh had a fun-filled day.
"Angie arranged for a few friends to join them at their house where they had trampolines and game booths like you see at carnivals," shares the insider. "Plus all of Shiloh's favorite foods like pizza, hot dogs and churros."
At the end of the day, Shiloh's like most teenagers. She's a good student and enjoys school. "She's very curious and likes learning new things," says the insider, adding that she's thinking about following in her parents' showbiz footsteps.
"Shiloh can see herself working behind the scenes in Hollywood, producing like her dad or directing like her mom," the insider says. "She's been around the world and has experienced a lot already, so her background and observations could really take her far."
She also loves hanging out with her friends. "She's been socializing a lot more in the last few years," the insider says of Shiloh, who counts Stranger Things actress Millie Bobby Brown, 17, as one of her famous pals.
"She's also close with Ellen Pompeo's daughter Stella," the insider shares. While she does hang with kids who don't have Hollywood connections, "growing up in the spotlight hasn't always been easy for Shiloh," adds the insider, "and it helps to spend time with people who get it."