Shiloh Jolie-Pitt's Best Red-Carpet Looks Over The Years

Thanks to the numerous red carpet events she attended, we got to witness just how much Shiloh Jolie-Pitt's style has changed and evolved through the years. Being the first biological child of former Hollywood it-couple Angelina Jolie and Brad Pitt meant that all eyes would be on her since day one — and everything Shiloh wore would be a topic of discussion.

"I don't tell the kids how to dress," Angelina Jolie revealed to Vogue in 2023. "Even when they were little, I just put things in front of them. Nobody has to go anywhere if they don't want to, and if they don't want to dress up, they don't have to." Jolie's approach to parenting and the freedom she allowed her kids to have is surely part of why Shiloh's style always seems so authentic and personal. From masculine suits to her mom's vintage dresses, Shiloh Jolie-Pitt has given us plenty of stellar red-carpet fashion moments, and here are our faves!

Celebrity kids are no strangers to borrowing iconic vintage outfits from their famous parents, and Shiloh Jolie-Pitt is no exception. In 2021, she attended the UK premiere of "The Eternals" alongside her mother and siblings. For the occasion, Jolie-Pitt went with a Dior dress from her mom's closet, one that Angelina Jolie had worn in 2019. To finish off her look, the teen went for subtle yet classy makeup and timeless golden hoops.

For the 2019 "Maleficent: Mistress of Evil" premiere in Rome, Italy, Angelina Jolie and her daughters Shiloh and Zahara Jolie-Pitt decided to go for a matching vibe by wearing all dark colors. For Shiloh, this meant black pants and a funky black jacket with subtle gold stripes. Shiloh — who has been known for her androgynous fashion — also rocked her signature short hairstyle with a deep side part.

At the Los Angeles premiere of "Paper & Glue: A JR Project" in 2021, Shiloh Jolie-Pitt decided to take a more casual approach to red-carpet fashion. She wore ripped jeans and a black hoodie, which she paired with a casual, messy bun. Over the years, the teen has given us a variety of fun fashion moments, but it's clear that she feels the most comfortable in a casual 'fit.

In 2014, Shiloh Jolie-Pitt attended the Los Angeles premiere of "Unbroken" alongside her father and older brothers. For the occasion, Jolie-Pitt wore a stunning black suit, which was similar to the looks her brothers went for. In 2010, Angelina Jolie revealed to Vanity Fair that her daughter loves masculine fashion. "[She dresses] like a little dude," Jolie said. "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."

In 2017, Shiloh Jolie-Pitt attended the Toronto International Film Festival with her mother and siblings. At the premiere of "The Breadwinner," the tween decided to go with a casual indie sleaze look — black jeans, a gray top, and a black and white plaid flannel shirt. Even though Jolie-Pitt tends to shy away from accessories, this time, she opted for layered necklaces.

For the "First They Killed My Father" premiere at the 2017 Toronto International Film Festival, Shiloh Jolie-Pitt went with a more classic look — black pants paired with a white button-up and a matching black waistcoat. To ensure the look wasn't too formal, Jolie-Pitt once again accessorized with her signature necklaces.

2021 was the year Shiloh Jolie-Pitt embraced more traditionally feminine fashion pieces, and one of those occasions was also the showing of "Eternals" at the Rome Film Fest. Jolie-Pitt showed up to the red carpet alongside her mother and sister. While all three looked fabulous, Jolie-Pitt showcased a new facet of her style in a classic black A-line dress, which she paired with edgy printed sneakers for an unexpected pop of color. The teen also opted to wear makeup, something she has been rocking more frequently in recent years.

In 2019, Angelina Jolie and most of her children attended the world premiere of "Maleficent: Mistress of Evil," and for the red carpet, every single Jolie-Pitt kid (who all have incredible style) dressed up according to their preferences. For Shiloh Jolie-Pitt, this meant dressing down a pair of black pants and a button-up with a leather jacket and sneakers. Her hair was in her at-the-time signature side-swept style, and she looked as happy as ever while supporting her mother.

For the Los Angeles premiere of "Eternals" in 2021, Shiloh Jolie-Pitt decided to once again scour her mom's closet in hopes of finding a piece that would speak to her. And indeed, the teen showed up to the red carpet in a Gabriela Hearst dress that Angelina Jolie had worn a few months before. To match the elegance of the dress, Shiloh's hair was styled in a loose updo with face-framing tendrils, and she rocked a bit of neutral makeup as well.

Shiloh Jolie-Pitt also attended the Los Angeles premiere of "The Breadwinner" in 2017, and she looked sleek and stylish in a head-to-toe black look. However, one thing we couldn't help but notice is that Jolie-Pitt also rocked a backpack on the red carpet — something we don't see too often. It certainly seems that when Angelina Jolie said she lets her kids wear whatever they like to events, she wasn't joking.