Shiloh Jolie-Pitt: From Tomboy to Lady

Discover Shiloh Jolie-Pitt’s transformation from tomboy to lady, and how she embraces her unique journey. Read more here.

Shiloh Jolie-Pitt is the first biological child of Brad Pitt and Angelina Jolie. Dating since 2004 while Brad was still married to Jennifer Anniston, the couple eventually married in 2014. Despite their ten-year relationship and six children, their marriage ultimately failed.

Shiloh Jolie-Pitt

In 2016, Angelina Jolie filed for divorce, citing irreconcilable differences, and sought sole custody of their six children without seeking child support.

At the time, her attorney told PEOPLE magazine: “Angelina Jolie Pitt has filed for dissolution of the marriage. This decision was made for the health of the family. She will not be commenting at this time, and asks that the family be given their privacy during this difficult time.”

Shiloh Jolie-Pitt


Pitt, on the other hand, stated: “I am very saddened by this, but what matters most now is the wellbeing of our kids. I kindly ask the press to give them the space they deserve during this challenging time.”

Born in Namibia in 2006, Shiloh, the Jolie-Pitts’ first biological daughter, captured the public’s attention. Joining older siblings Maddox, Pax, Zahara, and younger twins Knox and Vivienne, she became a cherished member of the family.

From a young age, Shiloh Jolie-Pitt gained notoriety for her tomboyish appearance, consistently opting to dress in masculine attire.


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Brad and Angelina prioritized their children’s independence, encouraging them to freely express themselves in interviews. They emphasized the importance of personal choices, whether in fashion or career paths.

When interviewed by Oprah Winfrey, Brad said: “Although she is a sweet little girl, she is always acting like a boy. She also dressed up like she was some John or Peter.”


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When questioned about her preferences, the actor stated: “No. It’s her choice, and we respect it.”

During an interview with the Daily Mail in 2007, Jolie revealed that Shiloh expressed admiration for her brothers’ hairstyles and expressed a desire to have a boyish haircut of her own.

She discussed Shiloh’s clothing choices, revealing a preference for jackets, ties, and slacks over skirts, dresses, and feminine attire. She said: “She thinks she is one of her brothers.”


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A post shared by Shiloh Jolie-Pitt (@shiloh_jp)

During Angelina’s movie premiere in October 2021, she surprised everyone by deviating from her usual attire of blazer, tie, and slacks, leaving the audience stunned on the red carpet.

At the “Eternal’s” premiere in Los Angeles, all six children joined Mama Jolie to show their support.

She stood out in a stunning tank dress paired with ballet sandals.


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A post shared by Shiloh Jolie-Pitt (@shiloh_jp)

Onlookers couldn’t ignore the striking resemblance Shiloh bore to her renowned mother, Angelina Jolie. In a striking departure from her previous styles, Shiloh Jolie-Pitt stunned with a new feminine look, ditching ties and slacks for a beautiful bun and posing alongside her siblings on the red carpet. Notably, Pax was absent from the event.

Her remarkable transformation caught the attention of viewers who praised her for resembling her mother more closely.

What do you think of Shiloh Jolie-Pitt’s change? Do you think gender non-conforming children grow free to choose to be as they want? Let us know in the comments.

Written by Dadadel

CEO of @dadadelcreative® | Social Media & Digital Marketing Agency
Software Engineering graduate • Copywriter • Digital Marketer

Dadadel loves to smile and have a fine bottle of red wine. She is very keen on sarcasm and cats.

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