My son the cross-dresser

Guest post by Sarah Tuttle-Singer

My son is big into tractors. He loves Lego. He builds skyscrapers out of wooden blocks, and then goes all Godzilla on them. He plays in the mud, and looks for bugs, and has a thing for dinosaurs. And on the first day of gan (preschool) last week, my son told me he wanted to wear a dress.

“This dress,” he said, reaching for the pink frock with the purple butterflies on it that I had ordered online over the summer. “This dress is great for twirling,” he added, touching the ruffles around the edges.

He was right. It was the dress perfect for twirling. And that’s exactly what he wore.

“Do you know your son is wearing a dress?” one father asked me during drop-off.

(No! Really? Must be laundry day, Captain Obvious, because you forgot your cape.)

“Maybe he wants to wear this instead?” a mother said, handing me a shirt from her son’s bag.

(Right, because nothing screams “manly” like a shirt with a yellow duckling on it.)

“Doesn’t he have boy clothes?” a grandmother asked when she saw my son twirling around in his flowery frock.

(No, lady, I’ve decided to exercise my God-given right as his mother to turn him gay, so it’s dresses or nada. Now, lets crank up the Madonna and get this party started!)

O.M. Hashem, people. Get a grip!

Yeah, my son is wearing a pink dress with ruffles and butterflies. But so fucking what? It doesn’t impede his ability to play in the dirt. He’s not tripping over the hem and hurting himself. Yeah, he’s twirling a little bit, but it’s awesome: he’s learning about rhythm and movement, and about the way soft fabric feels against his legs when he whirls around in a circle.

I didn’t encourage his fashion pick: believe you me, our drawers are stocked with clothes in navy blue, steel, and hunter green. We have shirts with pictures of dinosaurs and trucks and cartoon dogs emblazoned on the front. He has the requisite badass AB/CD (AC/DC parody) T, and when he was a baby, he rocked the “Chicks dig my Crib” onesie. But when my son gravitated toward his sister’s skirts and dresses over all the clothes in his drawer, I honored his choice.

Yeah, my son is only two-and-a-half years old, but this is one way I can let him (safely) exercise his autonomy. Sure, there are things that parents decide for their kids all the time: If asked, my son might have opted out of his brit, or the DTaP vaccine. But this is different.

And if anybody — parent, or teacher, or child — belittles my son for this, I swear I will fillet them. Because even if he starts breastfeeding dolls or asking to take ballet class, so long as he’s happy and healthy, then it’s all good. And I will honor his choice to wear dresses, or lip-sync to Like A Prayer or wear red nail polish on his toes.

Or fall in love with whomever he chooses.

(Although Little Dude better get his own high heels.)

We live in Israel, and in a country that places such a high premium on machismo it won’t be easy for my son. But in the meanwhile, he’s learning how to own his choices. When the older kids say “Why are you wearing a dress?” he says: “Because I want to.”

And when one of the savtas on the kibbutz had the nerve to speak to my son in female verb tense — knowing full well that he’s a boy — he said to her: “Stop it. I am not a girl. I’m a boy. And boys can wear dresses.”

And, guess what? Turns out my son is a trendsetter. A few days ago, another little boy showed up to gan in a purple tutu.

Comments on My son the cross-dresser

  1. I loved this article and all the comments! I remember on a ‘school spirit day’ in elementary school everyone was supposed to wear pink and the class with most participants got prizes. One boy in my class wore his sister’s pink dress because it was the only pink clothing they had in their house. And he got sent home from school 🙁 I don’t remember kids making fun of him, just the principal saying that it was ‘not allowed’. This was early 90s. So glad things are changing for a new generation!

  2. Love this! When I was a little kid, I hated it when my mom made me wear dresses. I always felt naked in girl’s clothes. Now I my husband and I share most of our wardrobe. There’s nothing wrong with being comfortable in what you wear.

  3. Awesome!! I posted a couple of pics of my 4.5 year old wearing dresses I had put away for his little sister to grow into, on Facebook last night & a lovely friend linked me this!
    My sons Dad hates when I paint the little mans nails or let him wear lipstick… so the dresses didn’t go down very well but I just keep telling him, denying the little guy a chance to have fun NOW, will only make it MORE attractive when he’s older!
    And even if it remains attractive, so what! Thanks for sharing this! Wonderful!! x

  4. Awesome!! I posted a couple of pics of my 4.5 year old wearing dresses I had put away for his little sister to grow into, on Facebook last night & a lovely friend linked me this!
    My sons Dad hates when I paint the little mans nails or let him wear lipstick… so the dresses didn’t go down very well but I just keep telling him, denying the little guy a chance to have fun NOW, will only make it MORE attractive when he’s older!
    And even if it remains attractive, so what!

Read more comments

Join the Conversation