The Day My Son Wore a Dress to School

So, it happened. The big day my sparkly 5-year-old middle son had been excitedly awaiting and the mama worry in my belly had been fretting. The day I would fulfill my son’s request and allow him to wear a dress to school. How would he be received? Would people be kind? Was I doing the right thing?

It was the perfect scenario, actually, in that fortuitous, twist of fate way that life has a way of spinning. My son had asked to wear a dress to school (detailed story here) the week prior and now: PAJAMA DAY!

Who doesn’t love pajama day? Being cuddly cozy all day at school, especially in the chilly winter months. It’s delightful. It also proved to be the perfect opportunity for my son to debut his usual nighttime attire. Not Batman pajama sets or truck-themed footed jammies like my 3-year-old son. Nope. My middle son regularly sports his sister’s outgrown sleepwear: princess nightgowns and pastel hued sleep sets.

So, after all of the carefully examined reasoning I’d conducted just days before which lead me to realize that the only logical, moral, and reasonable answer for the dress question was to allow it, I went about helping my son select his pajama day ensemble. A turquoise hued “mermaid queen” bathrobe over a pink princess nightgown with white sweatpants underneath. The reasons for the sweatpants were threefold: 1) it’s regularly in the 35°F range here this time of year and the kids have outdoor recess, 2) the school requires male students to wear pants, 3) our family has required our daughter to wear pants underneath nightgowns she sported to school pajama days because kids are in school to learn and play not to worry about or have their activities limited by wardrobe malfunctions.

And so, all weekend, the pajama day outfit laid neatly folded on my son’s dresser with the rest of his week’s school outfits. Each day he walked by the colorful pile of sleepwear, touching it wistfully with a gentle smile of anticipation.

On Monday off to school he went in his green button-up shirt, red bowtie, and red pants for “red and green day.” Amidst the holidays activities, he told everyone and anyone who’d feign listening all about his pajama day outfit. He told classmates and teachers, buddies and staff. He was proud. Excited. Fearless.

The next day came. Pajama day! As I sat in the dark pre-dawn of the morning sipping my coffee ahead of my daily home yoga practice, I heard the muffled thud of my kindergartner’s feet hitting the ground, the squeak of his bedroom door yawn open, the whisper of his sleepy footsteps padding into the bathroom. Minutes later he crept downstairs and stood silently, proudly, arms wide, chest lifted, grin broad, entirely dressed in his pajama day ensemble. He was effervescent. Beyond joyful.

“You look beautiful!” I whispered to him from the sofa, setting my near-empty coffee mug down on a coaster. He smiled. I opened my arms and lap, and up he scampered, curling in just right like only he knows how to do. And there we hugged and talked and watched a hairstyling video on YouTube — as per his request — before returning to the morning routine.

He left for school that day awash in excitement, bubbling with unbridled enthusiasm, enveloped in boundless optimism. I convinced myself to follow his lead, but there was a whirring in my belly wondering: “What if?”

“What if,” my inner worry asked, “children are unkind?” “What if,” it haunted, “he cries?” “What if,” it pummeled, “this dims his light and closets him?” “What if,” it persisted, “you were wrong?” Those tears, that pain, that mournful experience would rest on my shoulders, weigh my heart. It would stand — in my mind — as my fault.

I sniffed back tears, shook my head up high and countered my fear, “What if children aren’t unkind? What if he’s happy? What if this brightens his light? What if he’s accepted for exactly who he is? What if I chose right?” And I hushed my fear.

That afternoon at school pick-up I waited. Straining from my shrimpy 5’4″ (on a tall day) vantage point to see my son’s face as soon as he exited the building. My daughter exited first and my 3-year-old and I greeted her with a welcoming hug. Then we saw him, nightgown frills peeking out from underneath his winter coat.

He was beaming! Glowing! Brimming with happiness, still proudly sporting all the pastel layers of his pajama day ensemble.

“How did it go?” I asked him, kneeling before him, searching his blue eyes for truth. “Great!” He said. “Everyone was nice?” I asked, my knees chilled by the asphalt beneath me. “Yep!” He chirped, shimmying the straps of his too-big purple backpack onto his delicate shoulders. “No one said a thing?” I said, trying to muffle my surprise. He shook his coifed head.

I looked at him. Really looked at him. He was smiling wide with eyes sparkling. I deep sighed from the inside out. So off we went to the minivan as if it was any other day.

Because, as much as my worry had told me otherwise, that’s all this day was. It was simply a day, like any other day. Just with mermaid-princess pajamas, and a sparkly boy whose self-acceptance, fearlessness, and optimism proved that unfounded fear is no reason to hide, deny, or change. That concern over the unknown is not worth implying a child should be ashamed of or change who they are. That allowing my son to be who he is unfettered by my fears was the only way to go.

I let my son wear a dress to school, and it was one of the best decisions I have ever made.

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The Day My Son Asked to Wear a Dress to School

It had been a long day. Sunday late afternoon after a day of activity, I was putting away laundry in my 5-year-old middle son’s room while mentally reviewing my “new week preparation” to-do list when he asked the question. “Mommy,” he asked, poking his head up from underneath a mound of blankets on his doll-strewn bed, “can I wear a dress to school?”

I stopped arm in midair holding a handful of carefully folded princess nightgowns waiting to be stowed in his top drawer. My mind shuffled for an answer. “I don’t know, Bud. I’m not sure that’ll fly at your school.” I tucked the frilly pajamas into their home and closed the drawer. Grabbing a stack of mermaid printed t-shirts, I paused. I knew my answer was insufficient.

For 5 years this kid had known me and if he didn’t realize within that half a decade that antiquated policies were not going to stand as anything but fuel to my inner fire to tear down harmful, hurtful, double-standard walls so that all children can be better and have better and do better than we are and have and did, then he hardly knew me! But I wasn’t prepared to answer this. I was scared.

“Not that it’s right and not that it’s OK, but kids might say unkind things to you if you wear a dress.” I gently reminded him. “I know.” He said with a cool, unruffled calm I have never personally known. He asked again if he could wear the dress. I paused, trying to think as I sorted socks from skivvies. “I don’t know, Bud. Maybe you should ask your dad.”

Off he went. Ask he did. And he blindsided my husband entirely who, in his own surprise at the bold question, declined the request.

That night at story and circle time, my son brought his book selection to me: Who Are You? (a book about gender and identity.) And that solidified it. This wasn’t just about a dress. This wasn’t just some boundary testing. This was more. More than I knew how to handle.

All night and into the morning my mind spun. What did my mind say? What did my gut say? Why would I say “yes”? Why would I say “no”? I examined it all. And I realized that any inclination to deny the dress was rooted in fear. Fear for my son’s feelings. Fear for my son’s innocence. Fear for what children and adults may say or do. Fear for what this meant. Fear of the unknown.

But was my fear a good reason to deny my son’s request to wear a dress to school? Should my anxieties and insecurities, weaknesses and failings dictate my child’s path? Absolutely not.

Would I allow my daughter the freedom to fulfill such a request? Was I acting from bias? Yes. Shamefully, I noted my own double-standard. If my daughter asked to deny girly garb, would I deny her that? If she asked to cut her hair short, would I force her to keep her long locks? No. Sure, I would miss the dresses, the moments spent braiding her gorgeous golden mane, but this was her body, her life, her identity, her choice. My wants, fears, wishes, and insecurities should never trump her desires for her self. As long as she was not harming anyone and being thoughtfully safe in her choices, I would support her unwaveringly. And so I must do the same for my son.

I felt the anxious quiver of love-based worry fill my heart.

Speaking reason to my fear, I persisted in my internal questioning. Did I want to risk implying that my son should change, hide, or be ashamed of himself? Did I want to risk closeting him and all of the horrific statistics of self-harm that doing so entails? No!

I had supported him thus far, sewing him a mermaid tail costume — despite my complete lack of skill and genetic predisposition to be a horrid seamstress — when he asked to be a mermaid for Halloween. I had hunted for mermaid and unicorn t-shirts and swimsuits to suit his interests. I had pieced together a rainbow flying unicorn costume complete with a fabulous, flowing wig and pink feathered wings for this year’s costume. I’d found him ballet lessons at a wholly supportive dance studio. I’d signed him up for skating lessons when Johnny Weir’s sparkling performances made my son’s eyes widen with joy. My husband had fashioned him a portable hairstyling tray for his doll heads. I’d gone to bat for him, ensuring his school would be a safe, supportive environment in which he could learn, grow, develop, and thrive as an individual. We opened our hearts and home to his daily playroom drag performances. We had supported him wholeheartedly, fiercely, lovingly through it all. This was the next step.

So I realized that I had to say “yes”, whether or not I was ready. Whether or not people judged or balked or refused to understand. Whether or not I was brave enough to do so.

Because I simply had no solid ground, no formidable counter-reasoning to do anything else. Because I loved my son as I loved my daughter and wanted him to grow and thrive and love himself just as I wanted for my daughter. Because I’m a parent and sometimes being a parent means doing what’s right for our kids even if it scares every cell of our being. Because my son deserves to be who he is, whatever that may look like. Because my son deserves an unwavering ally in me. Because this is my child. Because I am his mother.

And this is our next step.