How Angelina Jolie Really Feels About Shiloh Jolie-Pitt's Sense Of Style

It's hard out here for a celeb kid. It's even more difficult when the celeb kid is a member of Hollywood's most talked about and speculated upon A-lister family. Despite only being 16 years old, Shiloh Jolie-Pitt has spent her entire life under the media spotlight, with the tabloids following and dissecting her every move. One of the primary focuses has been on Shiloh's unique sense of style. She's always been very determined in her choice of clothing.

During her formative years, Shiloh was a classic "tomboy," always dressing in what's viewed as traditional "boys" clothing, rocking suits and ties on the red carpet, and shunning frills and frocks. Per The Velvet Chronicle, the tabloids harangued the little girl with speculation —  and anonymous source-based reports that she was transgender or gender-dysmorphic. Angelina Jolie brushed off the rumors and gossip. She refused to label Shiloh or place her in a gender-conforming box. She made it clear it was nobody's business how Shiloh chose to identify. "I don't think it's for the world to interpret anything," Angelina told the Daily Mail. "She likes to dress like a boy and wants her hair cut like a boy." The mom-of-six said that Shiloh once even wanted to go by a totally different name. "She wanted to be called John for a while," Angelina shared.

 Shiloh's clothing choices have radically changed as she progresses through her teenage years. So, how does Angelina Jolie really feel about Shiloh Jolie-Pitt's sense of style?

When rumors started that Brad Pitt and Angelina Jolie were hooking up on the set of "Mr. and Mrs. Smith," they became an instant tabloid obsession. Both denied becoming romantically involved until after Brad split from Jennifer Aniston. Still, that didn't stem the flood of salacious headlines about Brad and Angelina's odd relationship. At the time, she was mom to Maddox Jolie and was in the process of adopting Zahara Jolie. Brad later adopted both children, in addition to Pax Jolie, in 2008.

"Before I met Brad, I always said I was happy never to have a child biologically," Angelina told Readers Digest. That changed, though, with the arrival of Shiloh Jolie-Pitt, the first of the couple's three biological children. "Shi's so full of light and love; she's just a little honey and very, very funny," Angelina told MSN (via People). "I think I'm recognizing some of myself in that one — she's going to be a little bit of trouble!" 

Shiloh's strong personality and style preferences were evident from the get-go. However, some people bizarrely claimed Angelina was responsible for her daughter's clothing decisions. "I think [Shiloh] 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," Angelina insisted to Reuters. "Society always has something to learn when it comes to the way we judge each other, label each other. We have far to go."

Angelina Jolie has always been unwavering in her support of Shiloh Jolie-Pitt's gender identity exploration. "[She dresses] like a little dude. Shiloh, we feel, has Montenegro style. It's how people dress there," the actor told Vanity Fair. "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." 

Some criticized Angelina for allowing her daughter freedom of expression. Media outlets cherry-picked comments from her Vanity Fair interview and jumped straight on the transgender bandwagon. As Salon notes, "New York magazine immediately capitalized on the headline that Shiloh 'wants to be a boy,' as did the Frisky and the Star." The website surmised that Angelina's "comfort " level with her daughter's refusal to follow societal gender roles likely made many feel uneasy.

"I have a very strong-willed 4-year-old girl who tells me what she wants to wear, and I let her be who she is," Angelina told Stylist magazine (via TooFab). "I want to do what's in her heart and what's in her heart is to dress like that. I think it's beautiful." 

As is customary with kids, Shiloh Jolie-Pitt is growing up fast. And as she grows, she continues to evolve in both looks and style. Although Shiloh stepped out on the red carpet wearing a dress in 2021 — with her long blond hair bunched up and even a smidge of makeup on her face — recent TikTok videos show that Shiloh still loves to rock a tracksuit, baggy pants, and oversized T-shirts while getting her dance moves on. However, she's replaced suits and ties with strappy dresses and sparkly shoes for red-carpet appearances nowadays. As she's matured, Shiloh's features have remained a mix of her parents. But, since she became a teenager, her looks have favored Angelina Jolie more, with her full lips and almond-shaped eyes. 

Shiloh's clothing also mirrors her mother's look, as does her sister Zahara's. And there's a reason for that. Vogue reports that the siblings have been raiding their mom's designer-packed wardrobes and "recycling" her vintage outfits and dresses. Shiloh and Zahara were rocking two of Angelina's forgotten frocks for the premiere of "Eternals." Zahara was clad in Angelina's golden-hued Elie Saab design from the 2014 Academy Awards, while Shiloh opted for her mom's old Gabriela Hearst "Quillaume" gown.