Angelina Jolie’s eldest daughter: From a tomboy with braces to a new generation of expensive beauty

Shiloh Nouvel Jolie-Pitt, the first biological daughter of Angelina Jolie and Brad Pitt, has recently turned 16 and is drawing attention for her stunning transformation.

Once known for her tomboy style and braces, Shiloh has evolved into a glamorous and confident teenager, sparking admiration across social media and entertainment circles.

Her natural beauty—marked by her mother’s expressive eyes and full lips—has made her a standout figure in the public eye.

Shiloh’s appearances on the red carpet alongside Angelina have only increased her visibility and fame.

Many are speculating that she may soon enter the modeling world, as reports suggest top agencies have already shown interest.

Her unique look and strong celebrity lineage give her a promising start in the fashion industry.

With the right guidance, Shiloh could become a powerful name in modeling, opening doors to awards, endorsements, and more.

As she steps further into the spotlight, the world is watching closely to see what comes next for this rising star.

While many of us feel 2021 was stagnant and that not much changed in the world, that certainly was not the case for Shiloh Jolie-Pitt.

Not only did Brad Pitt and Angelina Jolie’s 15-year-old daughter live her best life during the pandemic – catching private flights, attending film premieres around the world and shopping with her siblings – she also broke the internet with her dramatic style transformation.

Here’s how Shiloh made headlines and kept social media buzzing this year.

Shiloh Jolie-Pitt in 2017 vs 2021. Photos: Getty, VCG

Back in January, we found out Shiloh had undergone quite the makeover while in lockdown. Sporting denim cut-offs, pierced ears and long locks tied up in a bun, it was a far cry from the gender-bending tomboy outfits Shiloh had sported over the years.

Shiloh Jolie-Pitt attends the European premiere of Maleficent: Mistress of Evil at Odeon IMAX Waterloo in October 2019, in London, England. Photo: Getty Images

Fans were left confused by Shiloh’s new feminine look, especially after both parents mentioned during interviews that she thought she was “one of the boys” and went by the name “John”.

Jolie told Vanity Fair in a 2010 interview that Shiloh has been exploring gender since age three. “She wants to be a boy,” Jolie said. “So we had to cut her hair. She likes to wear boy clothes. She thinks she’s one of her brothers.”

Here’s why Shiloh’s subtle style change was only the beginning of a much bigger reveal.