Why Can’t I Find Decent Dresses For My Five-Year-Old Son?

The request came over breakfast a few weeks after school started. Our family had just moved back to Ontario after two years in Nova Scotia. We had navigated thousands of kilometres, a sea of cardboard boxes and all the stormy emotions stirred up by saying too many goodbyes and braving too many new things. The to-do list finally seemed near the end of its spool. That was until, between bites of his cinnamon toaster waffle, my five-year-old son, Finn, piped up.

“I know what we forgot to do, Mom!” He had an alarmed, exasperated tone that went up in volume when he flipped his palms skyward and splayed his fingers theatrically. “We forgot to buy my dress!”

I clutched my coffee, nodded and looked down at the table. I had not, despite all the rigmarole, forgotten to buy Finn a dress. I had just been hoping (for several months by this point) that he would forget about needing one.

I didn’t have a problem with Finn wearing a dress. The issue was that I was pretty sure the kind of dress Finn had his heart set on didn’t actually exist outside of his five-year-old imagination. I couldn’t fathom an explanation for this that would satisfy him. I mean, this is a kid who has traipsed through H&M many a time with his sister, a place where the girls’ aisles bulge with glittering unicorn headbands, sequined shirts and a slew of random, fantastical accessories such as long blonde braids and faux, pin-on cat tails. Who could blame Finn for assuming that, in this day and age, it’s entirely possible to buy nearly anything you can dream up? Especially when versions of that dream already exist in “girl” form?

That Finn wanted a dress wasn’t a surprise. He has delighted in modelling his sister’s accessories—hair elastics, plastic bracelets, dollar store rings—ever since he developed the dexterity to pilfer them from her room. At age two, he wore a pink plastic Minnie Mouse bead necklace for all waking hours (and, if I’m honest, also some naps, because taking it away wasn’t worth the meltdown). He learned the word “fancy” that year (as in “Look Mommy! I’m fancy!”) and put it to very repetitive use. He discovered pleasure in trying on my high-heeled shoes and making them “click click click” across the wooden floor. To attend a “Princess and Super Hero” tea party (a hospital fundraiser), he dressed as Disney’s Moana and collected an autograph from every princess in attendance. He couldn’t have cared less about the superheroes.

Throughout his final year at daycare, at every single drop-off, Finn pulled a Princess Elsa dress over his track pants and shirt before heading into the classroom. You could actually see his little shoulders relax as he donned those blue puffed sleeves; wearing the dress so obviously made him happy.

When Finn graduated from daycare Elsa was relegated to our dress-up bin. Sometime after, Finn told us he was done with the pretend kind of dressing up.

“Mom, I want a real dress. NOT a costume. One from the boys’ section. OK?” This was not so much a request as a directive delivered across the dinner table from a booster seat pulpit, Finn’s dark brown eyes laser-locked on mine. He nodded as though trying to hypnotize me into agreeing. I nodded back, despite the pit forming in my stomach over the herculean nature of this assignment.

While there are books for parents about boys who want to wear dresses and books for kids about boys who wear dresses (Morris Micklewhite and the Tangerine Dress is our family fave), there are no manuals for obtaining said dresses. Boys’ dresses—and I mean those of a non-cartoonish nature, but still with glitz, glam and a skirt worth twirling—aren’t found in stores. They aren’t really found anywhere.

Google “dresses for boys” and you will find a couple of links for kurtas, the long tunics worn by males in some cultures (but which are too plain for Finn’s taste—he told me that he wants his dresses to “look like Rihanna’s.”) Most of the Google results involve links for “dress fashion for boys,” which I interpret as the search engine’s kindly attempt to smooth what it assumes was a typing mistake in my query. “Dress fashion for boys” means vests, bow ties and suits, not dresses. But it wasn’t a typo. Why can’t I find dresses for boys?

I have to admit this lack of options originally surprised me. I mean, it’s 2020, an era in which blue suede loafers, sparkly dinner jackets and pink ties are widely available for grown men. The singer Harry Styles hit up last year’s Met Gala wearing a sheer black blouse with lace; the actor Billy Porter wore a black velvet tuxedo gown to the Oscars last year and a spectacular white feather train to the Golden Globes earlier this month. Gender fluidity is everywhere…except the kids’ clothing department, where, I would argue, we actually need it most if we’re going to raise children to accept gender fluidity as a norm.

Instead, at the mall, boys learn it is the most “normal” for them to wear clothes with boxy cuts, bland colours, sporty stripes. Acceptable graphics include vehicles, dinosaurs, garish monsters. There are no embellishments that mimic the sparkle or sequins found in the girls’ aisle unless the sequins are sewed on in the shape of something appropriately masculine (think animals or superheroes).

To be fair, there are more options now than ever before for gender non-conforming children. I was impressed by the company Primary, which makes awesome clothes for “kids” rather than boys or girls. The Canadian company Mini Mioche markets their luxury wardrobe basics as mostly unisex and this neat company, Princess Awesome and Boy Wonder, has been lauded for filling a void by making dresses in prints that are traditionally found in the boys’ section boy (dresses with pterodactyls, airplanes, solar systems and more). Their construction truck dress, called “Groundbreaker,” felt pulse-raisingly groundbreaking to me until I realized that it, and all their dresses with traditionally “boyish” prints and designs, are still meant to be worn by girls.

Not surprisingly, my search for a “real” boys’ dress was a fail. I was left with the question of how to explain to a five-year-old why clothing companies make lots of things for non-girly girls, but very little for boys who want to sparkle.

But the conversation we eventually had was less complicated than I feared. It went something like this:

Me [wary]: “Buddy, I haven’t gotten your dress because I can’t find any in the boys’ section.”

Finn [surprisingly]: “Oh! That’s OK! Why don’t we just get one from the girls’ section?”

Me [mega-relieved]: “That sounds like a great idea.”

And so Finn went on a dress-buying mission (with his dad, it turned out, because I was out of town). He chose a sleeveless, ¾ length, black velvet number with a cross-body ruffle. It also has rainbow glitter, and it looks great when he twirls.