My Son Wears Dresses And I'm Completely Fine With That

My Little Boy Wears Dresses And There’s Nothing Wrong With That

My-Son-Wears-Dresses-and-I-Will-Always-Be-Okay-With-That-1
Courtesy of Lindsay Wolf

On his first birthday, my son Everett wasn’t very concerned about the presents we gave him or the new clothes his extended family gifted him. He had one goal in mind, which was to wear his big sister’s unicorn princess dress. He brought the fabulous, poofy thing over to me with young determination and made a bunch of animal-like grunting sounds. Then he bowed his head, which is the surefire sign that he’s ready to stick something new on.

My Son Wears Dresses, And I Will Always Be Okay With That: little boy in dress
Courtesy of Lindsay Wolf

I immediately placed the dress over him, straightened it out, and watched with a smile as he gently and happily twirled around. While my son sashayed across the room, the last thing on my mind was seeing a boy wearing a dress. Here was a young, tiny human who hasn’t been pressured yet by society to conform, and he was doing something he loved. His gender was secondary to the pure joy on his little face, which made the moment that much more special.

My Son Wears Dresses, And I Will Always Be Okay With That: little boy in dress
Courtesy of Lindsay Wolf

As I witnessed Everett celebrate in the way that he individually wanted to, I realized something profound. Moments like this one have taught me that I’ve become the exact kind of parent to him that I have always longed for.

Growing up, I was fascinated with clothes traditionally worn by boys and went through a substantial phase of wearing them. I’d pull my hair back in a ponytail, put on my favorite baseball cap, and dig around for hours in the mud looking for bugs. I was in my happy place during those times, knowing full well that the world didn’t exactly agree with my desire to dress like my little brother. It became downright painful to stand out as I got older, so I started wearing dresses and makeup to fit in as best as I could. But the gender-curious kid inside was aching to keep experimenting.

My Son Wears Dresses, And I Will Always Be Okay With That: Three kids posing by tree
Courtesy of Lindsay Wolf

It’s no wonder that while I was juggling the inner conflict of both wanting to wear clothing made for boys and also wanting to be accepted by those around me, that I was also struggling deep inside to embrace my sexual identity. I was crushing on girls as much as boys, and I was crushing on them hard. My desire to wear different types of clothes, my growing preference for the ladies, and my ongoing struggles both at home and in school led to a ton of secrecy and shame.

As I grew up, I believed that the only way to exist as a woman was to look like the ones I saw in the media. The thin-bodied, makeup-laden, straight white females who graced the pages of magazines I loved taught me that to go against the grain would be a terrible failing on my part. And so, I became exactly what I saw. I pretended I wasn’t bisexual, I wore makeup all the damn time, and I went to dangerous lengths to keep myself skinny.

My Son Wears Dresses, And I Will Always Be Okay With That: two kids posing
Courtesy of Lindsay Wolf

Here I was appearing to be the poster-child for conventional femininity, and yet deep down I was absolutely miserable. Sure, people saw a positive, perky, enthusiastic woman when I was around them. You can thank my lifelong struggle with perfectionism and people-pleasing for why I successfully turned every fucking frown upside down. But underneath the false smiles, there was a heartache inside that eventually made itself present as I got older. It wasn’t until my stepdaughter, Bella, came into my life that I even stopped to question why I’ve been forcing myself to appease the world for so damn long.

My Son Wears Dresses, And I Will Always Be Okay With That: little boy in dress
Courtesy of Lindsay Wolf

Bella’s always been the type of kid who walks to the beat of her own drum, and this has been a huge source of inspiration for the late-blooming societal rebel in me. We’ve had many fun shopping trips that have involved going into both the boys and girls sections of Target, and we’ve occasionally left the store with clothes solely designed for men. I’ve been in awe of her profound internal knowledge that she didn’t want to allow outdated gender norms to get in the way of expressing who she felt she was. My step-kid has blown me away with her courage, her resilience, and her unwavering strength.

My Son Wears Dresses, And I Will Always Be Okay With That: baby in car seat
Courtesy of Lindsay Wolf

I’ve also seen Bella struggle at times when loved ones haven’t always agreed with or supported her self-expression. I think the challenge of not being able to always protect her from that ignited a fire in me to give my two biological children unwavering acceptance. I’m a proud mama bear who openly teaches my kids that families come in all genders, sexualities, identities, conditions, and sizes. I’m the mom who will always let my daughter pretend she’s Spiderman and make believe that she’s married to a girl. I’m the mother who will happily and easily stick a dress on my young son anytime he asks for it.

I was also once the girl who was afraid to be completely herself. And I am now the woman who bravely came out to the world last year.

My Son Wears Dresses, And I Will Always Be Okay With That: two kids posing
Courtesy of Lindsay Wolf

Our children are being raised at a time when so many external forces are incorrectly teaching them about their worth. Our societal conditioning has them believing that their inherent value exists outside of them, and this is so dangerously wrong. What’s more, they are exposed to media imagery that still has a long way to go in terms of diversity and inclusiveness. As parents, we need to start being loving influences in their lives as early on as possible. We’ve got to start seeing our kids as full-bodied human beings who deserve to shine in their own unique way.

We have to let go of any expectations we may have had about who we thought they’d turn out to be. Because when we do, we miss out on their undeniable magic and even worse, we risk totally dimming it.

My Son Wears Dresses, And I Will Always Be Okay With That: little boy in swing
Courtesy of Lindsay Wolf

Everett is 15 months old now, and he still enjoys wearing his sister’s clothes. My husband and I still love watching him dance around in them. Whether or not this means that my son will explore his gender identity in new ways as he grows, I don’t know. What I do know is that I will always have his back, loyally support him, and unconditionally accept whoever he wants to be no matter what. I will be his safe harbor to experiment, make mistakes, and discover his interests. I will forever grow into exactly the kind of mom he needs and wants.

My Son Wears Dresses, And I Will Always Be Okay With That: little boy in dress
Courtesy of Lindsay Wolf