Shiloh Jolie's Laid-Back Hoodie Style Evolution

Like mother, like daughter! Angelina Jolie has proven multiple times that she knows how to dress for revenge, and her daughter's wardrobe is becoming just as iconic. Angelina and Brad Pitt welcomed Shiloh in May 2006, and it didn't take long for them to realize that she was one of a kind. As with the rest of the Jolie-Pitt children, Shiloh was thrust into the limelight from a very early age. As she was growing up, the paparazzi's snaps of her raised a few questions.

"I think she is fascinating, the choices she is making. And I would never be the kind of parent to force somebody to be something they are not. I think that is just bad parenting," Angelina said to Reuters in July 2010. By that time, Shiloh had been expressing herself as a tomboy, rocking a pixie haircut, little suits, cargo shorts, you name it, but she always had the unbridled support from her mother.

"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," Angelina said later in the interview. As she's grown up, Shiloh Jolie has undergone quite the style transformation, from comfortable classics to punk rock 'fits. She spends the majority of her time as a professional dancer and choreographer in LA, which we all know has a very specific style. There are lots of baggy clothes, lots of dark neutrals: right up Shiloh's alley. Hoodies have been a staple in Shiloh's closet for a while now, but she's certainly transformed the way she styles them, so let's take a look back at her laid-back style evolution.

While on a family trip to Paris, France, in July 2021, Shiloh Jolie perfectly exemplified how to style the perfect look using the sandwich rule. She started with a black hoodie with a small white graphic, pairing it with black-and-white Vans. She finished off the look with khaki pants and a black face mask, and tied her blond hair back into a bun. We're not sure how Jolie made it through the summer day without melting, but anything goes in the name of fashion!

The Jolies took another trip across the pond in October 2021, but Shiloh Jolie was still rocking a similar ensemble. For this day abroad, she paired a black crewneck sweater with denim shorts and yellow-and-black high tops, appearing to take a break from the hoodie for a minute while still maintaining that relaxed aesthetic. As with the rest of her siblings and mother, she finished off the look with a black face mask. While she paused on the hoodie front, Jolie continued her quest toward comfort dressing.

In November 2021, Shiloh Jolie returned to her hoodie game and amped it into high gear when she decided to wear one to the premiere of the "Paper and Glue" documentary. For the red carpet, she decided on a cropped black hoodie with metal details on the sleeves, ripped, high-waisted blue jeans, and purple Converse, once again pulling her hair back into a bun. It seems as though the dancer was getting her footing when it came to styling, making intentional decisions about proportion and just the right amount of edge.

Over the next three years, Shiloh Jolie largely maintained a quiet, private life, but we finally saw her in one of her iconic hoodies again. In 2025, she appeared to have graduated from the plain hoodies. She was spotted running errands in Los Angeles that February wearing a "Scarface" hoodie with the hood pulled up, baggy blue jeans fastened with what looked like a shoelace, and white sneakers. She paired the look with an oversized black backpack, making for the quintessential errand-running outfit, if we say so ourselves.

A hoodie is probably one of the most versatile garments out there; they can be dressed up, dressed down, or dressed inconspicuously, even. Shiloh Jolie proved that she knows how to give off "cool girl" vibes while being dressed down, and we're taking notes. Later in February 2025, Jolie was seen wearing her signature ensemble while running errands once again. This time, she wore a gray hoodie and paired it with black sweatpants and white sneakers. You know you're a pro once you can make sweats look chic!

Shiloh Jolie may have the laid-back hoodie style down to a science, but she'll always remember where she came from. In March 2025, she was once again seen in the streets of California rocking a (you guessed it!) black hoodie with a large white graphic on it, matching black cargo pants, sneakers, and of course, that black backpack. She makes them look so punk-rock and effortless that we're just patiently waiting until she releases her own line of hoodies.