Why We Need to Talk About Shiloh

(even though we shouldn't need to)

Note to readers: I started this op-ed over a year ago, not long after Shiloh’s sartorial transition. But I never finished it. Last year, a non-profit asked me to write about Shiloh for their website, and I finished a version, but then felt that, as a journalist, I shouldn’t be writing for specific groups because I wouldn’t be able to write about their group if I did so. So I decided to send it out to various outlets—The Washington Post, The New York Times, the usual suspects. Never, in all my years of writing op-eds, has one been rejected so quickly. Any theories on why?
—LD

It was 2008 when Brad Pitt announced to the world, via Oprah, that his almost-two-year-old daughter, Shiloh Jolie-Pitt, child royalty of the world’s most gorgeous movie stars, wanted to go by a “male” name.

Her mom, Angelina Jolie, later said, “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.” The Today show’s headline was: “Angelina Jolie says Shiloh ‘wants to be a boy.’”

The family’s attitude seemed to be: Whatever. It’s no big deal. And the press followed their lead. The story of Shiloh-turned-John was of interest in our celebrity-focused culture, but it wasn’t an obsession, and news outlets didn’t announce that Brangelina were the parents of a transgender boy.

When, in 2021, at age 15, Shiloh appeared on the red carpet at a movie premiere in a khaki tank dress—a style we might call “haute military”—there was no obsession, either. Few media outlets made a big deal of the revelation that the era of boys’ suits, short hair, and the name John had been a phase. Like millions of tomboyish girls before her, Shiloh had spent years edging closer to the male gender role and had a change of heart—or maybe just a change of style—during puberty.

In a less polarized world, and one in which there wasn’t an ongoing gender culture war, Shiloh’s transformation wouldn’t be remarkable. And it shouldn’t be. But we do need to talk about it, because Shiloh’s trajectory can teach us something important about how we treat and understand gender stereotype-nonconforming children.

Shiloh was born before the concept of the transgender child was seeded into the public consciousness. She announced her proclivities only a year after the country’s first pediatric gender clinic in America opened, and six years before Time magazine declared a “transgender tipping point.” There were no school lessons on preferred pronouns and transgender identities. There were no death threats to pediatric gender clinics, nor did governments engage child protective services agencies to investigate parents because they either did or did not socially or medically transition a child with gender differences or distress.

Shiloh was not declared to be transgender and facilitated toward a new identity. As far as we know, her parents didn’t tell her that she truly was male, but rather they accepted her stereotype nonconformity and acknowledged her as more like her brothers than her sisters. Perhaps when Shiloh’s proclivities were announced, there was still some lingering consciousness of the tomboy heyday of the 1970s and early 1980s, when masculine looks for girls were accepted and even encouraged, when we battled to give girls equal rights to sports and education. Even back in 1950, The New York Times reported, “‘Tomboy’ Phase Called Natural.”

More importantly, social transition, in which prepubertal children are facilitated to live as the opposite sex—to call themselves by male or female pronouns or stereotypically male or female names, and embrace the stereotypes associated with the opposite sex in clothes and hairstyles—wasn’t a common practice. Schools weren’t secretly socially transitioning children without parental knowledge, nor were people insisting kids would kill themselves if they couldn’t socially transition.

Yet had she been socially transitioned, her trajectory might have been quite different.

A recent paper suggests that the practice of social transition greatly increases the likelihood of medicalization—while previous research suggests that if not socially transitioned, the vast majority of kids who identify as the opposite sex will grow out of it and not desire medical interventions. The UK’s National Health Service recently issued new guidance for children with gender distress, noting that, “in most prepubertal children, gender incongruence does not persist into adolescence.” The document adds that “although there are differing views on the benefits versus the harms of early social transition, it is important to acknowledge that it should not be viewed as a neutral act.” Rather, it should be seen as an “‘active intervention’ because it may have significant effects on the child or young person in terms of their psychological functioning.”

Thus, “social transition should only be considered where the approach is necessary for the alleviation of, or prevention of, clinically significant distress or significant impairment in social functioning and the young person is able to fully comprehend the implications of affirming a social transition.”

Perhaps the media ignored Shiloh’s switch because it interrupts the oft-repeated narrative: a child’s rejection of both biologically-based and societally-created gender norms indicates something larger about their identities; gender nonconformity is synonymous with transgender identity; and kids who aren’t allowed to or didn’t transition are in imminent danger. Parents of very young kids are now regularly accepting their children as transgender and socially transitioning them—even without psychological support—often when they are like Shiloh, even if they don’t have gender dypshoria.

There is no clinical test, no way to know, for whom a cross-sex or transgender identity is a phase and for whom it’s permanent, nor for whom social and medical transition is the best path or not. Most former tomboys I’ve interviewed, who had very similar childhood’s to Shiloh’s (minus the fame and riches) told me that puberty was an excruciatingly uncomfortable period of getting used to their changing bodies, but, like most people in the scientific literature, they eventually became comfortable. Some were straight women. Some were gay. Some of the younger ones transitioned, because the technology was available, and were happy. But many older former tomboys told me that they would have leapt at the chance to transition had that technology been available to them, and they were so glad that they hadn’t, that they’d come to accept and love their female bodies.

Even the tomboy heyday wasn’t as accepting as it could have been. Most masculine girls were pressured—by their parents, by the culture—to surrender that masculinity at puberty. That tomboy phase The New York Times endorsed was for ages seven to ten. For some kids, the end of that phase was when it got really hard—when it became clear that their masculinity was not a costume they were wearing, but something innate that they didn’t want to tamp down or deny. Meanwhile, there has never been in this culture room for feminine boys to be themselves—and telling them that they can be or are girls doesn’t actually create that room, though it may indeed bring more immediate psychological relief.

In a perfect world, girls like Shiloh wouldn’t have to surrender their masculinity, ever—but would feel free to if they wanted to. Nor would a feminine boy ever need to suppress that part of himself. In a perfect world, what kind of body you have, male or female, wouldn’t have to be inextricably associated with certain toys or colors or personality traits. In a perfect world, Shiloh’s choice of suits or ballgowns wouldn’t be news. But we haven’t yet done the cultural experiment of deemphasizing gender, curbing the messages that tell kids there is one set of colors, toys, personality traits and activities for boys and another for girls, and to access them you either must be born into that category or transition into it.

Shiloh’s story should show us that we can’t forecast the future based on childhood gender stereotype nonconformity. It shouldn’t have to be told—but, for now, it should be, so that kids can learn that it’s okay to embrace or reject stereotypes as much as and whenever they want. We can love, support and accept people who transition, but always make room for kids to explore gender without denying or rejecting their bodies.

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