My Boy Dresses Like a Girl and It’s No Big Deal


More and more mothers are proudly sharing photos on social media of their sons heading off to school dressed in traditional ‘girls’ clothes. I asked one Toronto mom of two boys (ages 6 and 8) who happily encourages their desire to dress in girl’s clothing about the reactions she receives—not only from other parents and teachers, but their peers too. If you have a child that likes to dress in opposite ‘traditional’ gendered clothes, this is a must read! It’s brutally honest and inspiring. Kudos to Mom!

When did they start wearing girlsclothes to school?

My boys have been dressing up their whole lives. It really started with Harry, my eldest son, who is eight years old. He was about 2 when it began and so was Dan. Dan was really just copying what Harry was doing. We let the boys dress up because we feel its a big part of growing up. We feel that role playing is important to creativity and growth. Dressing up has been a gradual progression for Dan. He will find something that he likes and then its a thing he does for a while. Wearing a skirt started as a dress up day for school, so my husband made him a skirt for that day. He liked it and had fun, plus nobody bothered him so he felt comfortable to continue. He went from hand me down boys clothes to feeling like he could pick pink shirts and shorts. Weve never judged him, so he never judged himself and the best part is that no one at school really did either. Dressing up is something all kids enjoy doing. And so they should. It also doesnt necessarily mean they will continue to do so throughout their lives. I think thats something we need to remember. Same goes if we had a daughter. If she came to us and wanted to dress up as lets say, Batman, we wouldnt discourage that either. Society tends to want to label people. Lets think on that for one second. When we do that, it changes who we are. Why would we want to do that?


Did you talk to the teachers about this before school started?

When our eldest Harry was in JK, we spoke to his teacher to let her know that he enjoyed dressing up and we were okay with that. She let us know that her classroom was an open free environment where you could be who you wanted to be. Shes an amazing teacher and so is her teaching assistant. He did like to wear a hoodie on his head that was tied up in the back to look like a ponytail. He always wanted long hair so he would never take it off. Andthere was nail polish. He loved having his nails painted. I loved that about him too. The teachers were very supportive but Harry let it all go in about the middle of the JK year. The boys were relentless with him, so much teasing, so he decided it was better just to wear his hoodie and nail polish at home. That made him so sad. You could see it in his face. It was hard on my husband and I. Here we were, trying to teach him to be himself: authentic, original, happy. The kids were changing who he was. But, in the end, it was his decision. Dan started the same way in JK. Wearing the same hoodie on his head and the nail polish. So cute. His teachers were the same teachers Hudson had so we just said, Dan is like Harry and loves to dress up too,and they loved him just the same.


Were their classmates understanding?

Im not sure if they were understanding or if just curious as to what he was doing? He was experimenting and they were wondering why? Why does Dan wear nail polish? I thought only girls are allowed to do that. So many questions from all the kids. Were those questions answered at home? Who knows? For us, we got asked questions from our kids too. Mom, can I try on your high heels? Sure, why not? Dan had to explain a lot to the other kids, and the teachers helped him. They had to keep reinforcing that all the toys in the class were for everyone to play with and there werent girl toys and boy toys, just toys. That went on for a while. Dan plays equally with boys and girls, he just doesnt tend to like a lot of the toys and games most boys tend to play. He tends to play with dolls, or play house with the other kids. Hes really inclusive and doesnt limit himself. He only came home a couple of times and said someone asked him if he was a boy or a girl because he was playing with a doll. He said, Im a boy and I like dolls. Sometimes it was frustrating for him, but at the end of the day he was being himself and playing with the toys he liked. I admire him for that. Looking that question in the face and saying Im me and Im going to keep being me, because this is what makes me happy. Dan has told me he’s a boy who just likes to wear girls clothes. He has said to me many times, Mom Im not a girl. Im a boy and these are the clothes I like to wear. I cant argue with that.


Did you get any looks from other parents? Are they understanding? How about teachers?

The parents in the neighbourhood are great. We live in an amazing part of Toronto. All sorts of families live in our hood. There are two-dad families, two-mom families, single-parent families and so on. So, with that said, I haven’t come across anything other than warmth and love. Being a part of a warm, open, creative community is a big part of our values at home. Our neighbours are amazing and all of the parents really rally around each other. We feel lucky to be where we are. I’m sure there are people that don’t see things the same way we do. That’s normal. I would just hope that they would keep that to themselves, because what my kids do should be their choice not anyone else’s. If you look around, for a moment, you might see other kids wearing superhero costumes at the park, or maybe their pajamas to a party, those are other parents allowing their kids to choose what they wear outside the house. It’s just self-expression and I think should be encouraged.

My husband and I tend to have our own fears about what other kids will say. A perfect example is yesterday afternoon he walked up to a friend’s house where there were four of his male friends all playing in a garage. My husband said he had a moment of fear come over him as Dan was in pigtails and barrettes. Will they make fun? Then one of his friends spoke up and said ‘Hey Dan, want me to get you a popsicle?’ Like nothing, like he didn’t care, or didn’t notice. That’s pretty amazing. I think we tend to underestimate our kids and how accepting they can be. I have no idea why he’s instantly accepted and why Harry was teased for being an individual. Is it personality? Is it confidence? Whatever it is he’s got it. That makes us happy. 


How did you explain to him there is a chance some people may not understand?

We have always warned our kids about people not understanding self-expression. Especially when they were little. Little kids have lots of questions, because they are curious. Once, one of Harry’s friends asked me why Harry likes to wear nail polish. My answer sort of took him by surprise. All I said was that rock stars like to wear nail polish and that one day Harry wanted to be one too. He looked at me, then looked at his mum and said, I want to wear nail polish too then. That made me happy. Why are we ok with adults standing out, or being their own person and not kids? What are we so afraid of? It’s just another part of being a creative person. I think the more self-expression the better. Without it life would be so boring.


Do your sons like clothes shopping?

Both of my sons love to shop. Love, love, love. They explore everything. Harry just goes off and comes back with a ton of stuff he loves. He’s got an amazing sense of style. (I think he takes after me, of course). Dan loves just going into the girl’s sections and rummaging through the hairbands, barrettes, necklaces and everything. He’s always loved dresses and skirts. He loves fashion. I love that he loves fashion. I just let them explore and come back with what they’ve found. Then we go through and see what’s appropriate or not too expensive. I try to keep Dan in check sometimes. Not too girly. We just wanted to take it slow. Work up to it. Of course I’m still aware that not all people are nice or accepting. Even though most people think he’s a girl because he’s got that most gorgeous face, that’s been going on since he was born. Sometimes I don’t correct them. It would be just too confusing and I don’t want Dan to get hurt by what they might say. Even though I know he can handle it, I don’t want that for him, not at six-years old.


What do you want to say to other parents of boys who just like to dress like girls, or, for that matter, girls who want to dress like boys? 

The only thing we can say is, for us, self-exploration is a positive thing. The earlier you find out who you are, and what makes you happy the better. Some people take a lifetime to find out who they are and what makes them happy. Why not speed up the process? We just try to love them as much as we can and let them lead the way. I don’t want to come across all hippy dippy, I’m just saying maybe we should just let them lead when it comes to creativity and self-expression. In the end I think the kids are teaching us a thing or two about life. Why should it matter if we wear a dress or pants? When a girl chooses to wear a baseball cap, pants and runners we don’t say anything to her. I never had a doll. It wasn’t my thing, but no one asked me why I didn’t play with dolls? Why? If I was playing with a truck no one came up to me and questioned what I was doing. Why question a boy with a doll? Why does gender come into play when it comes to toys?

Do your sons play with boys’ and girls’ toys?

My boys have never liked to play with trucks. I’m not sure why but, we never questioned it. Harry’s interests have changed since he was little. He used to love the play kitchen and pretend cooking, but now he prefers Lego, Minecraft and Pokémon. But that was his choice, not ours. Dan really does like dolls. I’m not going to lie. He really does have a lot of Barbies. He loves changing their outfits and figuring out who’s going to wear what. He has many playdates with his friends too. They trade doll outfits, Barbie’s, Shopkins, whatever. All the parents have been amazing to him too. So much love and acceptance has really helped him and us. He’s really friends with a good mix of girls and boys. They love him all the same. He’s an amazingly, loving, kind, generous child and I think that’s why he has so many friends.

Why do you post photos? Is it to inspire and hope that others can relate?

Why do I post? That’s a good question. I don’t post often. Sometimes I’m hesitant. I’m scared of what people might think. Asking me hard questions about my choices as a parent, but I think there’s something bigger here than just me and my boys. The world is changing rapidly, faster than ever before. Sometimes change is scary, especially when you don’t know what the future might bring. So, with that said, I wanted to put it out there. I’m so proud of my son and the strength he brings to this world. He has taught me so much about myself and the world. My husband and I are in unknown territory. We’ve never done this before. That’s where we all are. Parenting is a scary place. Do we really know what we’re doing? Does anyone? Do we just do what everyone else is doing? Follow what our parents did? Or grandparents? OR do we let things just be as they are and see what happens. In the end it’s a choice. You can choose to be happy or you can choose to just be. I want everyone to see how happy our kids are, and how happy we are. In the end isn’t that what life’s all about? 

Tell me about your Dan’s very long (enviable!) hair?

Ok, to be honest he’s never had a haircut. He won’t let us cut it. We really have tried over the years to try to convince him to cut it, but nope, he insisted on no cutting. So whatever, his hair keeps growing, the pigtails are a very new thing. Just a couple of weeks ago at his birthday party he wanted them. In the past he said he wanted them but then I said no as everyone would think he was a girl and ask him questions about it. Then…… he said let’s do it. No one said anything and here we are. He still insists he’s a boy who just likes to dress up. No big deal. I think we all need to learn something from that. 


Leave a Comment