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A Boy and His Dress

by Joelle Wisler
Photo by: Shutterstock

This is the story of my own Princess Boy. Remember that book? Well, the mother in that story whole-heartedly embraced her son’s decision to wear a dress. And she even wrote a book about it. And went on press tours. And filled his closet with sequined, frilly gowns.

And in these ways made me feel like the worst mother ever.

This is the challenge I didn’t count on when becoming a mother.

I had prepared myself for the lack of sleep, and tantrumming toddlerhood, and knowing way too much about another human being’s poop.

But I wasn’t prepared when my three-year-old son decided that he wanted to wear a dress. And be a princess. Or a mermaid. Or a fairy. Like, every day for approximately two years.

The dress obsession began after he decided that Mama Mia was his favorite movie. There is a scene where the daughter in the movie throws off her dress and dives into the water with her bathing suit on. He spent countless hours perfecting this very move, using the back cushions of our couch as the ocean.

At the same time he was moved by Abba, he was also moved from the toddler room to the preschool room at daycare. The new, older girls in his class took a shine to him and gave him the role of the “baby princess.” He loved every pink tulle moment.

At home, he began scouting out his own perfect ensemble. And I have to admit I helped him find the right thing, not realizing the future depth of his devotion. What he chose was this white linen tank top of mine, with red flowers on it and a flowy bottom hem. The straps were so long that the neck of the “dress” settled just below his belly button. As a fashion statement, it was all wrong, but he was absolutely in love with that shirt. While wearing it he could become anything from a fairy princess to his mom at the beach.

After he had staked his claim to my shirt, I tried to wear it one day. Every time he looked at me he couldn’t stop laughing, saying, “You’re wearing my dress, Mommy!”

I would love to say that I was always 100% okay with him wearing a dress. His dad could have cared less what our son wore, and I should have, too. But I found myself creating arbitrary rules surrounding it that were more like little mirrors of my own comfort level. The main rule was that he couldn’t actually go out in the dress. I selfishly decided I couldn’t handle all the questions. He was pretty enough to be mistaken for a girl all the time anyway.

And at Christmas, let’s just say the princess dolls he wanted so badly did arrive and…so did their castle. Except that it was actually a Batman castle. He took one look at it and promptly turned the super secret escape hatch into a closet for fancy dresses and shoes.

I also found myself trying to justify his dress-wearing if a friend was over and saw him in all his sashaying glory, singing and dancing to the Rapunzel soundtrack. “It’s just his princess phase,” I once said, and laughed as she assured me her son wore fingernail polish for two years.

And then one day…

He was at the babysitters with a couple of little girls. The mother of the little girls came to pick them up and spied my son dressed from head to toe as Tinker Belle, proud as could be. The mom pulled the sitter aside and said,

“So, what are his parents DOING about that?”

And the sitter-who I will always love for saying this-simply said,

“Embracing it.”

I hugged her when she told me this, and in my mind I vowed to myself to be better at doing just that.

Well, this year Kindergarten came and with it, a day when my son came home with his sweatshirt zipped up just about as far as it could go. I knew that under that sweatshirt was an iron-on t-shirt that he and I had just made. On the shirt was a pink monster with wings and braces and it was awesome. And he was beyond proud of it.

“So, what’s with the sweatshirt, bud?”

“Oh, I zipped it up because one of the other boys told me my shirt was a girl’s shirt and I didn’t want anybody else to say that.”

With THAT:

Well, a) I wanted to go all mama She-Bear on that other kid and his parents.

And, b) My heart broke for my sweet little boy, who loves to bike and ski, but who also LOVES pink, just like his dad. The boy who learned to swim under water only because he desperately wanted to be The Little Mermaid.

That sweet kid who gave his baby sister the middle name Rainbow, and who actually cried when I packed away her newborn clothes because he missed her being that small.

So, as I felt my heart break that day he came home, I began to tell him over and over again how WONDERFUL he was and how AMAZING his shirt was and that OBVIOUSLY that other boy did not have any REAL fashion sense and….and…

and he put his hand on my knee and he looked at me and he said,

“It’s okay Mama.”

And he went and played.

Joelle is a writer, a mom, and an occasional physical therapist. Her blog is more free-range and less helicopter, more organic than processed, more mountains than city, and more hippy than hipster – Joelle Wisler.

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