Shiloh Jolie's Stunning Style Transformation

Brad Pitt and Angelina Jolie's daughter, Shiloh Jolie was born in Swakopmund, Namibia on May 27, 2006. The young Gemini has fascinated the world ever since, largely thanks to her extremely famous mom and dad and big brood of siblings. Shiloh resembles the perfect blend of her A-list parents, with her blonde hair and big blue eyes. Considering the world's collective obsession with Brad and Angelina, it's no wonder their kids have become celebrities, too. After all, Angelina is a bona fide movie star, channeling old Hollywood glamour in every look. Even without makeup, Angelina makes headlines for her beauty, taste, and influence. So naturally, we love staying in the loop when it comes to their kids. 

Shiloh's younger sister, Vivienne Jolie, has undergone a stunning transformation, both in terms of her style but also her legal identity. After Brad and Angelina's very public 2016 divorce, it seems like many of the kids have shed their dad's influence over their lives. In August 2024, after Shiloh turned 18, she petitioned to drop Pitt from her last name and the request was granted by a Los Angeles Superior Court judge, keeping only Jolie as her surname. Vivienne also dropped Pitt from her last name. So there are big changes for these kids, and Shiloh herself has undergone a remarkable transformation.

In February 2009, Brad Pitt and Angelina Jolie took their kids to the Lunt-Fontanne Theatre to see "The Little Mermaid" on Broadway in New York City. Pitt was seen carrying Shiloh Jolie, who was still just a youngster. They brought their older children, too, including Maddox Jolie-Pitt, Pax Thien Jolie-Pitt, and Zahara Marley Jolie (twins Vivienne and Knox Jolie stayed at home that night). The bunch of kiddos seemed nonplussed by all of the attention they were receiving, looking happy and relaxed. 

Shiloh, who was two and a half at the time, looked particularly peaceful and engaged. To add to the cuteness, Just Jared noted a sweet fashion moment from the night. Shiloh was wearing a cream, button-up sweater on the outing, and it was the same sweater that her big sister, Zahara had been wearing just a week before when Angelina took Zahara and Shiloh out for a shopping day in New York City. Anyone from a big family knows the reality of sharing clothes with siblings, and for these kids, that trend is no different. 

In 2010, while speaking with Vanity Fair, Angelina Jolie admitted that she dresses her daughter Shiloh Jolie "like a little dude." Elaborating on her daughter's style, Jolie said: "Shiloh, we feel, has Montenegro style. It's how people dress there. She likes tracksuits, she likes [regular] suits. She likes to dress like a boy. She wants to be a boy. So we had to cut her hair. She likes to wear boys' everything. She thinks she's one of the brothers," (via Glamour). Shiloh certainly did go through a tomboy period as a kid. At red carpet events, young Shiloh emerged with short haircuts and suits with ties. Judging from the family's use of hand-me-downs, we've got to wonder if Shiloh was rifling through her big brothers' closets for looks. It's great that her parents were so supportive of her sartorial preferences. 

When Shiloh Jolie was young, she wanted to be called John or Peter. Dad Brad Pitt told Oprah Winfrey about Shiloh's self-proclaimed name change during an interview. "She only wants to be called John. John or Peter. So it's a Peter Pan thing," Pitt told Winfrey, per HuffPost. "So we've got to call her John. 'Shi, do you want...' – 'John. I'm John.' And then I'll say, 'John, would you like some orange juice?' And she goes, 'No!' So, you know, it's just that kind of stuff that's cute to parents and it's probably really obnoxious to other people."

In October 2017, Shiloh joined her mom Angelina Jolie at the premiere of "The Breadwinner" at the TCL Chinese Theatre in Hollywood, California. Shiloh emerged in an all-black suit with a backpack, accompanied by Angelina, who wore a white dress. The two certainly made a cute, supportive pair.

In October 2021, Shiloh Jolie joined some of her siblings at the London premiere of "Eternals" to support mom Angelina Jolie. The whole family looked charming, but Shiloh in particular delighted fans by wearing one of Angelina's old Dior gowns. Angelina had originally worn the black and white printed Dior dress as a floor-length piece at a press conference in 2019 for "Maleficent: Mistress of Evil." For this later occasion, the dress had been altered for Shiloh to reflect a teenage wearer. The dress was knee-length, making it more youthful. Angelina was a huge fan of Shiloh's reworking of her gown, sharing with E! News, "I'm like, 'Oh my god, wear it and wear it better than me! And take it, and it's your turn, anything.' I'm that mom." Clearly, Angelina didn't mind one bit that Shiloh wanted to alter one of her gowns. 

In October 2021, Shiloh Jolie joined her mother Angelina Jolie at the after-party for "Eternals" in London. Shiloh revived some of that tomboy taste by wearing a black top and black shorts with black Converse Chuck Taylor All-Star shoes. She finished things off with a cool, sheer blue jacket that mimicked denim, complete with edgy detailing. She kept her look simple by wearing her hair up and removing the big, gold hoop earrings that she had worn on the red carpet earlier in the night. Angelina opted for a more glamorous afterparty ensemble, by wearing an emerald green caftan and nude pumps, with her hair down long. They were joined by sister Zahara Jolie, who wore a bright yellow mini-dress with off-the-shoulder sleeves. It was the same dress that Zahara had worn on the red carpet earlier that night, so she clearly loved her outfit. The trio looked festive and cohesive, while still allowing each personality to shine through.