My Son Wore a Dress for Picture Day, and It Reaffirmed My Faith in Humanity

I’m grateful to know that my kid’s teachers are willing to go the extra mile to make their students feel comfortable and confident.

Alex Richards
Apparently
4 min readNov 13, 2019

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Photo: Orbon Alija/Getty Images

As parents, we devote ourselves to protecting our kids. We stock the cabinets with food and clothes and medicine; we carry band-aids and books and water bottles; we do our best to shield them from danger.

But what about the things we cannot protect them from? Or, maybe, should not?

For me, this moment came when my 5-year-old son asked to wear a dress to his school picture day. He saw his 8-year-old sister try on her dress, and was so mesmerized by the sight of her twirling around the living room, that he asked for the same dress in his size. I was excited and proud of his choice. I strive to raise open-minded kids and to help them understand that we live in a world that is ever-changing, full of differing family structures and gender orientations.

That being said, when I ordered him the matching dress, I worried.

I live in Brooklyn in a fairly progressive bubble. But what about everyone else? It’s one thing for my son to don a frilly frock and wear it to a close friend’s birthday party on the weekend, or take a flannel nightgown to pajama day at his peace-loving preschool, but they wear uniforms at his new elementary school. We’re talking about 300 kindergarten through fifth-graders. A school full of strangers.

So, yeah, I worried.

I debated bringing it up with my son. Gently warning him that people might be mean, and that some people in our society are still narrow-minded. But that seemed like an unnecessary bubble-bursting effort.

Instead, I emailed his new kindergarten teachers. I was nervous, not knowing what their personal philosophies might be. What if they ignored my email, or worse, shut me down? Not that I was searching for praise. This was more of a heads-up to alert them of my son’s decision, and to express my hope that they might be accepting of it while also keeping an eye on the other kids; possibly intervening if any bullying or negative comments did occur.

Instead of the yeah, sure, I was expecting, the teachers surprised me.

After some careful deliberation, they held a “preferences” conversation at morning circle a few days before picture day. It was a simple conversation, one that five-year-olds could relate to: Some people prefer eggs, some cereal; some people prefer dresses, others pants; some like pink, some blue. They did not direct the conversation at my son, but when they mentioned it being okay for boys to wear pink, he raised his hand.

“I have a pink jacket!” he told the class.

The teachers gasped. “You do?! Will you get it right now and show us? Try it on!”

I’m told that when he came back to the circle with his pink jacket, he slid into it as though it was a mink coat. He beamed as he zipped the zipper, twirled as he snapped the snaps. After school that day, he mentioned the conversation.

“Guess what!” he said. “At school, we talked about how it’s okay for boys to wear dresses — and I already knew that!”

Now it was my turn to beam. I honestly couldn’t have wished for anything better.

Picture day finally rolled around. My son wiggled into his dress, a lovely Parisian number with stripes on the top and bicycle-patterned a-line skirt on the bottom. My breath caught in my throat as I sent him off to school, but I knew I had to let him go. That’s what we do, right? Raise them as best we can and then let them out into the wild?

Having recently read a story about a young boy being sent home for wearing a dress because it “distracted the other students,” I prepared myself for the worst when I picked him up from school. But the worst never came.

He was still in his dress, still smiling. The teachers mouthed a big, It went great! along with a thumbs up as I took him out of the classroom. As he told me more — and the teachers confirmed — I learned that most people hardly noticed his outfit choice, though some gave him compliments. There were a few looks, a few Why is he wearing a dress? comments, but my kiddo was prepared.

“It’s what I prefer,” he said, and went back to his ABCs.

As my children get older, I will continue to support their preferences, whatever they may be.

I have no idea if my son is gay or if he will grow up transgender or nonbinary. I honestly think he liked the feel of the material, and that he enjoys emulating his big sister. But I will be thrilled and up to the task if he does find himself outside the heteronormative box. I’ll read the books, join the groups, and keep talking to his teachers. I will support him.

It’s a tough world out there, but I am grateful to know that my kids are at a school where the teachers will go the extra mile to make their students feel comfortable and confident.

I am grateful to my kids for being their true selves.

And I am grateful to the lovely Parisian dress that helped me remember what parenting is really about.

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Alex Richards
Apparently

Alex Richards is a young adult author (ACCIDENTAL, ’20) and freelance magazine contributor living and writing in Brooklyn, NY. https://alexrichards.org