Why I Let My Kids Dress Themselves

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I remember walking through the aisles of my favorite kids’ clothing stores, picking out some of the sweetest things I had ever seen—tiny Mary Janes, sweater vests, the smallest pair of cords. I was excited to play dress-up with my kids. And at first, before they could walk, talk, or even move, really, I did. They had matching outfits and accessories—damn, I even bought my daughter a faux pink fur coat. My boys wore all of those sweater vests. It was ridiculously fun until it just became ridiculous.

The day came when my boys cried at the sight of a sweater vest. They preferred their Tom Brady jerseys and thermal pajama bottoms, worn inside out and backwards of course. When my oldest began to realize that I was dressing him and his sister in coordinating outfits, that shit didn’t go over very well. I worked up a sweat trying to get my daughter in her car seat with that pink fur number on. Oh, and those itty-bitty Mary Janes? As soon as she could get to them, she would take them off and throw them at me.

Kids enjoy playing outside. They spend most of their time on their knees, pushing things with wheels around. They like dirt, sidewalk chalk is king, and their pockets get filled up with rocks and worms. They wipe their noses on their sleeves. They wouldn’t be able to keep a pair of jeans from getting holes in them if the knees were patched with tar.

Naturally, it soon became too much work to coordinate perfect outfits for my kids. All the cute little accessories I had purchased for my daughter’s hair got sucked into some bottomless chasm with all the matching socks. And once my kids mastered the art of taking their clothes off, that is exactly what happened as soon as I forced them into their matching ensembles.

My boys told me those cute cords, khaki pants, and distressed jeans I had so meticulously picked out (to match their sweater vests) chafed their butt cheeks and made their wieners feel too squished. They prefer shorts with knee socks or sweatpants, you know, so things can be free to flop around. These are sometimes paired with a tucked in button-down shirt. Believe me, it is a look, and they dig it.

This is why I stopped caring how my kids dressed. The reality is that they want to wear what makes them feel like a rock star. Sometimes that means your son only wants to wear mismatched pajamas and a tutu. I think it’s fabulous, and so do they, especially when they get to go to the grocery store wearing their chosen outfits. The compliments they receive are heartfelt, and I can see it makes their heart sing.

Seeing that, I had to laugh at myself and their pretty little clothes (which were never even complimented by the way). It made me realize how unimportant it all is. My kids have wanted to dress themselves for a very long time, and I stopped caring if their clothes matched. Hell, I don’t even worry if their shirts are on backwards.

We have all been that girl or boy who has worn all of our favorite things all at once and felt like we could rule the world. For some kids, there is a tiny window in their life where they feel that free and confident; they don’t give a damn if their shoes go with their pants, because they have shit to do.

And really, when they have a chance to jump into a giant mud puddle, they don’t care if they are wearing their favorite dress or pants. It doesn’t matter if the superhero cape or the fairy wings get wet. What matters is that they feel awesome.

The other day my daughter asked me to paint her nails. Then, you know what she did, she went outside, climbed trees, and played four square with our neighbors. When she came in, her nails were smudged and smeared. She wore them like a badge, as she should.

When I see a child wearing torn jeans or a dingy shirt, I see so much more than that. I get to peek inside their lives. It means they are living. They are feeling. They are experiencing. They are rolling around in their beautiful childhood. They are escaping into a fantasy land that we all remember. How can you do that without getting dirty? Without getting torn up a bit?

Now that my kids are a bit older, I do have a few rules. I don’t want to see 6 inches of boxers peeking over my tween son’s jeans. But if it is 4 degrees out and he decides not to wear a coat, more power to him. If my 10-year-old daughter comes downstairs wearing leggings as pants with a tank top that does not cover her bottom, while sporting wedges, we are going to have a problem. However, if she wants to wear the same sweatshirt three days in a row, with her favorite (mismatched) knee socks and shorts, so be it. I will not try to talk her out of it. Now that I’ve been at this parenting gig for a while, I’ve learned which battles to pick, and what my kids want to wear is not one of them.

Clearly we are not in Paris, and this is not Fashion Week. I want my kids to express themselves, and dressing the way they feel is one way to do that.

Some of my best memories—some of their best memories—have been made at my sister’s house where we grown-ups sip wine or tea as our kids zip through the living room with their cousins, sometimes dressed as half superheroes/half clowns, dripping with jewelry. Pure joy.

And if I am being honest, I think it would be deliciously fun to wear yoga pants, my Metallica T-shirt, and a tiara to the grocery store.