Shiloh Jolie is channeling her mom circa 2002 with a new platinum blonde hairstyle that looks straight out of Life or Something Like It. The 19-year-old was spotted in New York City’s Little Italy neighborhood looking, as usual, like the spitting image of Angelina Jolie.

In the photos, Shiloh can be seen wearing a black hoodie, navy pants, and black tennis shoes. Her hair is pulled back in a sleek side-part. As for jewelry, she sported a bottom lip piercing called a labret, per The Daily Mail.

Much like her five siblings, Shiloh typically avoids the spotlight. Angelina explained her kids’ disinterest in fame during an interview at Santa Barbara International Film Festival this past February.

“I always wanted them to be around film because I wanted them to know…” she said, her People. “It’s such a wonderful family, to be creative, to be an artist, to be… [but] they’re not interested.”

The Maria actress went on, “They really don’t like any of the celebrity part of it, especially Shiloh hates it. I think in a very healthy way they don’t … It’s not a normal thing. It’s a silly thing really.”

That said, Shiloh’s little sister Vivienne has dipped her toes into the world of show business. The 17-year-old served as a co-producer and assistant alongside her mom on the 2024 musical adaptation of The Outsiders.

“She’ll correct me,” Jolie revealed during production in an interview with People. “She’ll say, ‘Didn’t you read the memo? We have to do this. We have to go through this.’ She’s been a really tough assistant.”

Angelina Jolie’s Daughter Shiloh Opts For First Transformation After Moving Out

Angelina Jolie‘s daughter, Shiloh Jolie, has chosen a look to accompany her new era!

The actress’s daughter switched up her looks for a bolder style as she stepped out over the weekend, months after she moved out of her mom, Angelina Jolie’s, house to live with her girlfriend.

Shiloh Jolie made waves last year when she famously dropped her father, Brad Pitt’s, last name in favor of her mother’s last name as soon as she turned 18.

Angelina Jolie’s Daughter Oozes Confidence On The Streets Of Manhattan

The 19-year-old was spotted looking like a completely new person while she stepped out to grab a few things at the San Gennaro Festival in Manhattan’s Little Italy. She showed up looking every inch a diva with platinum blonde hair and a prominent lip piercing.

Shiloh’s piercing reportedly resembles the early 2000s style of Christina Aguilera and drummer Travis Barker. The piece of jewelry dangled on her lower lip as she kept her makeup very edgy with a smoky eye.

The actress’s daughter opted for a casual look, featuring a black, oversized hoodie, baggy navy-blue jeans, and sneakers. Shiloh’s freshly dyed platinum hair stole the show as she styled it in a side part. The Daily Mail reported that she enjoyed the company of her close friend, Keoni Rose, during the outing.

The ‘Salt’ Actress Found Shiloh Jolie’s Independence Upsetting

The movie star has never been ashamed to speak about motherhood and display her undying love for her children; however, Shiloh’s decision to find solace outside her mother’s mansion left her feeling low.

The Blast reported in July that Shiloh had temporarily moved in with Keoni to live together in a shared apartment in Los Angeles, where they had been residing for a few weeks at the time. Shiloh and Keoni were also spotted outside their shared apartment running a few errands.

As for Angelina, it took her an unusually long time to acknowledge the thought that Shiloh was truly gone because she had gotten used to having her kids around.

However, Shiloh’s freedom from her next is not without her putting some safety precautions in place, as a close source noted that her kids have ex-Navy SEAL security personnel as bodyguards.

A Deeper Look Into Shiloh And Keoni Rose’s Close Relationship

The pair have been spotted multiple times in each other’s company, although they have not disclosed the nature of their relationship – whether platonic or romantic.

Last November, Keoni and Shiloh were spotted grabbing lunch together in Los Angeles. Keoni and the actress’s daughter ate their meal on the street as Keoni got comfy on top of her car while Shiloh stood nearby.

The pair gave the press things to discuss after Keoni brushed hair off Shiloh’s face while being super affectionate. By May 2025, Shiloh and Keoni set off dating rumors after spending the 19-year-old’s birthday with loads of PDA and shopping visits to stores in Los Angeles.

The close pals were also photographed getting some moves in at a dance studio in Los Angeles and then ate lunch with a few friends later in the day.

Brad Pitt Was Hopeful For A Reconciliation With The 19-Year-Old

Following the estrangement between Angelina and Brad after an unpleasant airplane episode in 2016, their kids have found themselves picking sides. Last year, Shiloh made her intentions official by filing for a name change in court, where she gets to adopt Jolie’s previous name and drop Pitt.

As reported by The Blast, sources close to Brad affirmed that the actor was less than impressed about Shiloh’s decision, even though he had seen it coming for years. Brad spent the last few years hoping for some reconciliation between his kids, and Shiloh’s action dashed those expectations.

The sources added that Brad is fully aware that while some of their adopted kids may shut him out forever due to their lack of understanding, he still deserves a few chances at being part of his biological kids’ lives.

The actor has, however, expressed his undying love and support for his daughter, stating that he is always within reach should she need any help.

Angelina Jolie Sees Life Outside The United States Borders As Her Happy Place

Now that the philanthropist has finalized her divorce from Brad and settled the custody arrangement for their six children, she is focused on the next mission in her life.

Insiders confirmed that the actress plans to leave the United States as soon as her last two children turn 18, in search of a happier place to live. The actress reportedly has her eyes set on several locations overseas, where she will find joy after leaving Los Angeles.