Boys in Dresses and the Differences That Define Us

It started with pink. As a tot, my son loved the color—he’d paint all pictures pink, then careen down the street on a red-and-pink trike, a pair of fuchsia Crocs on his feet. My wife and I didn’t care what color he gravitated toward, but a handful of people did. Like a boy at the farmer’s market, who pointed at Felix’s trike and declared it “a girl’s bike.” Or the group of teens who yelled, “Is that a boy or a girl?” while walking past our stoop.

As Felix grew older and left the protective bounds of our house for public school, we felt it best to equip him with the language to discuss his decisions, and concepts to inform them. We taught him that sex is biological and typically based on physical body characteristics at birth. Gender, however, is conveyed through style and behavior. It’s a concept created by society, and human ideas about gender differ over time and place. To give just one example, Scottish kilts may read to contemporary Americans as feminine because they look like skirts, but they were worn by male warriors till as late as the Second World War.

A person’s gender doesn’t necessarily say anything about their sex, and it certainly doesn’t indicate anything about who they are as human beings: their value, their abilities, their personality. Felix sees me, his male dad, putting on eye makeup when I go to parties, for instance, and he sees his female mom with greasy hands from doing home repairs.

This period of Felix’s life, from the age of 4 to 6, was an education for me too in how stares, eye-rolls, and barbed comments broadcast gender expectations to children when they reach a certain age. What’s taken as a toddler’s idiosyncrasies read quite differently in a kindergarten classroom.

One morning at drop-off, 5-year-old Felix angled his head upward for a kiss goodbye, but when I bent down to meet his lips, a woman interrupted us by exclaiming, “He’s too old for that, Daddy!” I was so taken aback, I didn’t know how to respond.

As Felix moved further into boyhood, his adventurous style developed, bolstered by the many adults in our community, who encouraged him to express himself and have fun doing so. My wife and I didn’t just humor him; we followed suit. When he asked to paint his nails, for instance, a friend and fellow parent told us about Piggy Paint, which is nontoxic. A week later, our whole family sported sparkly pink and aquamarine toenails. Next, Felix and his best friend decided to grow their hair out so they could wear it pulled back. And then came the day, right before he turned 7, when he asked if he could get a dress, just like Mommy.

To not directly address issues of gender stereotypes with him at this point felt irresponsible. I imagined him coming home from first grade, pale cheeks blotched with tears, his ego hurt by taunts, and his confidence in me weakened: “Why didn’t you warn me I’d get picked on, Dad?” I understand we live in a sometimes terrible world, where kids and adults are bullied and harassed because of their differences. Diversity, experimentation, and nonconformity scare some people, and children—our social barometers—may parrot their parents’ prejudices on the schoolyard.

I carefully couched my language with Felix though, knowing all too well how a parent can snuff out a child’s confidence in their instincts. I didn’t want him to feel like he was doing something wrong by desiring a dress. This is especially essential for our hypersensitive children, who so often read correction as criticism. I know I certainly did.

When I was growing up in the 1980s in a heteronormative, working-class home and attending a conservative Catholic school till eighth grade, the ways in which I was instructed to express my masculinity were as omnipresent and insidious as the second-hand smoke from my dad’s heavy cigarette habit. Big boys didn’t cry, hug, or dance. Nor did they stand out in any other way, except when on the sports field. The first time I watched Prince perform the song “Kiss,” while the credits rolled on Entertainment Tonight, I spun and gyrated over our living room carpet, mimicking his funky moves. My dad was not amused. Prince sang in a falsetto, appeared to be wearing a blouse, and expressed a frank sexuality that my father found as uncomfortable as I did compelling. When Welsh crooner Tom Jones covered the same song a couple of years later, my dad said, “It’s nice hearing a man singing it.”

As I reached adulthood, I began challenging these rigid masculine rules. At Oberlin College, I grew my hair long, dyed it red, and pinned it back in barrettes. I routinely wore dresses to parties for a couple of years, feeling more confident and beautiful—more myself—in women’s clothes. For now, I’ve adopted a somewhat androgynous look, mixing makeup with tight pants and patterned button-ups.

As experimental as I can be, my son is decades ahead of me in his comfort at blurring gender lines. When his mom took him to Target to purchase that dress he requested, he was at first surprised to find they’d have to go to the girls’ section, then accepted it without rancor. “That’s because it’s uncommon for a man to wear a dress,” he said, matter-of-factly.

He selected a pink-patterned dress for both its color and comfort. The first time he wore it to school, I went in for a class party at the end of the day. One of Felix’s male teachers, with tears in his eyes, told me how Felix was unfazed when some of the older kids made fun of him for dressing like a girl. Simply, without anger, Felix raised his palm in the universal sign for stop and said, “Let me be me.”

“Your son is so brave,” his teacher said.

And I agree, though he’s also extremely privileged. He has parents who have no qualms when, for example, he wants to dye his hair hot pink to match his sandals. He’s fortunate to go to a school that values the “whole child,” where the staff support students’ physical, emotional, and social development as much as their academics. It’s a very warm environment. When I emailed Felix’s teacher a heads-up that he’d be wearing a dress to school, she assured me he wouldn’t face any teasing in her classroom. Nor did he meet much aggression on the generally accepting streets of New York City, where he wore his dress on a long walk from downtown Manhattan across the Brooklyn Bridge.

“The first time I walked outside in a dress,” he told me, “I was kind of scared, but a lot of people in my class actually—surprisingly—liked it and complimented me, and that made me feel good.”

If only every child could grow up in a community where they could confidently express themselves in whatever means they want, gender norms be damned. There tends to be more leeway for girls on this front because patriarchy and masculinity are so dominant in our culture that a girl acting like a stereotypical guy—whether a so-called tomboy playing sports or a power-suited businesswoman in a conference room—isn’t always seen as negative.

Boys in dresses are another thing entirely. This challenges the status-quo by implying femininity is something our boys should aspire too, that femininity is equal in power and dignity to masculinity. And so Felix’s style results not just from our open-mindedness, but our feminism too. He’s seen his mother head off to her job every workday since he was a baby while I stayed home with him. Up and down our block live powerful, accomplished women of many professions—why wouldn’t he want to model himself on them? It’s just like, after seeing Star Wars: The Force Awakens, he pretended he was Rey on the playground.

If you have a boy at home interested in adopting traditionally feminine styles, this may be a natural result of the child seeing women as equal agents to men, and of their awareness that gender trappings shouldn’t be traps, hemming people into particular roles society at large believes they should play. It does not mean that your child is expressing gender dysphoria: that he emotionally and psychologically identifies as female. Nor does it say anything about his sexual preferences. Truly, our children can be as inconsistent as the weather in their likes and dislikes. Since the autumn has arrived, Felix has set aside his dress and sandals in favor of tight jeans and saddleback shoes, though his curly locks are still long and rose-hued, and the remnants of nail polish shine on his nails.

If your community isn’t a safe space for your child’s gender exploration, create that place at home. Be sensitive in your language and withhold judgement. Our style, the way we present ourselves to the world, says something about who we are and our values, yes; but it does not solely define us. It’s something to take pleasure in and enjoy and have fun with—not something over which to worry. That starts at a young age with sensitive, open-minded parents.

I can think of nothing more joyful than seeing Felix running down our block at twilight, his pink sandals sparkling on his feet, his dress streaming behind him, his face beaming with joy. Watching him, I feel optimistic about a future where there isn’t boys’ clothes and girls’ clothes; there’s just clothes, and we care more about the values and the attitudes of who we model ourselves on, and not whether they appear masculine or feminine.

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  • Marlana Sherman

    Your son is very brave. I do not know if I would have had the courage to do that as a child or as the age I am now. It is also nice that he is being raised and educated in a community that is very acceptable of his exploration of things.

  • sisterrocki

    it was so nice reading this piece. thank you.

  • Quiet Revolution

    How do you encourage your kids to confidently express themselves?