The 3-year-old's tomboyish look has tongues wagging, and last week's cover of Life & Style magazine asking, "Why Is Angelina Turning Shiloh into a Boy?"
But one parenting expert thinks everyone should simmer down and let the child be a child.
"What Shiloh is doing now at 3 is very age-appropriate," Michelle Golland, a clinical psychologist and MomLogic.com expert, told ABCNews.com. "Kids take on different identities. And she has older brothers. In some ways, she's going to aspire to be like them."
"Life & Style is way off the mark with this outrageous coverage," Rashad Robinson, GLAAD's senior director of media programs, said in a statement. "Perpetuating gender stereotypes and targeting children for ridicule about the way they dress is unacceptable."
But Glenn Stanton, director of Family Formation Studies at the conservative organization Focus on the Family, had a different reaction upon seeing the photo of a boyish Shiloh on the cover of Life & Style.
"I was shocked," Stanton said. "I thought, 'What in the world are these parents thinking?' It's very possible they are living in a fantasy world, where gender is only an appearance. If so, it's a very anemic view of what gender really is.
"This little girl Shiloh needs to be able to identify with what she is in her soul, in the deepest part of her humanity. They do her no favor by saying you can change lanes anytime you want in in life," Stanton said.
But psychologist Golland said gender identity and, particularly, sexual orientation at Shiloh's age are very fluid.
Golland's own son wanted to wear dresses and plastic Barbie heels between the ages of 3 and 4 after his little sister was born. She and her husband allowed him to and now at age 9, their son would probably deny that he ever wore girl's clothing.
For some children, however, this is more than a phase. In those cases, identifying with the opposite gender is hard-wired and unlikely to change. Golland recommended that their parents seek guidance and support from therapists familiar with gender variance and gender-identity disorder.
More Than a Phase?
Stanton acknowledgeed that gender identity-disorder exists but said parents need to step in and be directive. "Not scold, but gently lead and guide them in what they are, what God and nature has given them," he said. "It's not pushing the child, scolding the child, it's molding the child, enticing, leading the child in the way they should be."
It's much too early to know if Shiloh's apparent boy obsession is more than just a phase, Golland said.
Pitt once said his daughter only wanted to be called by a boy's name.
"She only wants to be called John. John or Peter. So it's a Peter Pan thing," he told Oprah Winfrey in 2008. "So we've got to call her John. 'Shi, do you want …' -- 'John. I'm John.' And then I'll say, 'John, would you like some orange juice?' And she goes, 'No.'"
Mother Elise Crane Derby, founder of Elisesramblings.com and a contributor to LA Mom's Blog, said, "Maybe when she's seven or eight, she won't be John anymore. Or maybe she has a bigger issue. On any front, it's better to let the kid be who she wants to be."
Kristin B. Dunning, who writes a blog called Well Read Hostess and contributes to Philly Moms Blog, said, "She'll most likely grow out of her interest in having a 'boy' haircut and wearing 'boy' clothes soon. In the meantime, good for her parents for letting her be who she is, especially challenging, no doubt, in the face of the constant public scrutiny."