When Brad Pitt was spotted in Paris on Feb. 23, it looked like he and Angelina Jolie had adopted a new child -- an adorable blond boy. Instead, it was the couple's 3-year-old daughter, Shiloh, sporting boys' clothes and a new haircut so shockingly short it immediately ignited a firestorm of controversy. "It's a drastic change," says an eyewitness. "The last time we'd seen her, her hair was longer and blonder, and she was more girlie. We were surprised Angelina dressed her so much like a little boy."

Reaction on the Internet was far harsher and even some seen-it-all celebrity stylists were stunned by the transformation. "Shiloh is pushing the boundaries of a tomboy look and crossing over to cross-dresser territory," Alana Kelen, senior fashion stylist at VH1, tells Life & Style. Celebrity stylist Gili Rashal-Niv agrees. "I get that times are tough but does Angie really need to have Shiloh sharing clothes with her brothers? Hopefully we won't be seeing Maddox in one of Shiloh's dresses any time soon."

It's just the latest sign that Shiloh's more comfortable doing traditionally boyish things. After all, Brad once said that his daughter responded only to boys' names. "We've got to call her John," he told Oprah Winfrey, noting that when he started to ask, "Shi, do you want..." she would interrupt with "John. I'm John." Then, Brad continued, "I'll say, 'John, would you like some orange juice?' And she goes, 'No!'"

Some parenting experts think that indulging Shiloh's masculine behavior is a mistake. "Little girls have never been women before," Glenn Stanton, director of Family Formation Studies at the conservative organization Focus on the Family, tells Life & Style. "They need help, they need guidance of what that looks like. It's important to teach our children that gender distinction is very healthy." But others think letting Shiloh wear what she wants is a vital part of learning to form her own identity. "Giving preschool-age children the freedom and flexibility to experiment with how they want to be seen in the world is a wonderful gift," parenting coach Karen Deerwester, author of The Entitlement-Free Child, tells Life & Style.

For more on Shiloh's shocking transformation, pick up the new issue of Life & Style, on newsstands now.