Dress for Yourself: What I Want My Daughter to Know Before Middle School

Today, I was window shopping for my daughter, who is heading into middle school this year. And while I was walking around, I saw this beautiful young Black girl wearing this big, dramatic, almost vaudeville-style outfit with headphones on.

My immediate thought was: "Wow. Good for her."

It wasn't an outfit I would necessarily pick out for myself. That wasn't the point. What struck me was how confidently she seemed to be wearing something that was so distinctly her.

And it made me think about how differently I approached clothes when I was her age.

When I was in middle school and high school, the goal wasn't to figure out who I was. The goal was to figure out how to look like everyone else.

How do you conform?

How do you avoid sticking out?

How do you make yourself as small as possible so nobody has a reason to scrutinize you, tease you, bully you, or point out that you're different?

I was already a bigger, taller girl. I couldn't exactly disappear into a crowd. But I certainly learned to try. And underneath all of that conformity were messages I didn't even realize I was absorbing:

You're too big.

You stand out too much.

You stick out like a sore thumb.

It's not okay to be completely yourself.

And eventually, "make yourself smaller" stopped being metaphorical for me.

For a period of my life, I developed an eating disorder. I literally tried to make myself smaller.

What if our kids don't have to learn that lesson?

Now I'm a mom sending my own daughter into middle school, and I'm thinking about what messages I want to give her instead.

And one of them is this:

Dress for yourself.

Wear the thing that makes you feel like you. Maybe that's whatever is currently trendy at school. Maybe it's jeans and a T-shirt every single day. Maybe you love dresses, or maybe you hate dresses. Maybe your personal aesthetic looks like it fell out of 2026, 1996, or 1896.

I don't know.

I've had people tell me in therapy that they feel like their personal style belongs in an entirely different time period. I've met other people who desperately want to feel beautiful or handsome in the clothes that are fashionable right now, but those clothes just don't feel right on their bodies.

And maybe we don't have to make that such a big fucking deal.

They're clothes.

As long as your outfit isn't stabbing people as you walk by, we're probably okay.

We Were Taught to Conform

I actually think we're living through an interesting cultural transition.

Many of us raising kids right now grew up with the message:

Don't stick out. Fit in.

Don't give people something to make fun of.

Don't be too loud.

Don't be too weird.

Don't be too much.

And now we're trying to raise children with a very different message:

It's okay to be yourself.

That's harder than it sounds when many of us still carry the scars of what happened when we stood out.

Sometimes what looks like judgment is actually old fear.

We learned that being different could be dangerous socially, so when we see someone confidently being different, part of us may instinctively want to pull them back toward conformity. We tell ourselves:

"Don't wear that. People will look at you. And what will they think?"

But maybe instead of teaching the next generation to fear being noticed, we can teach them how to survive being seen.

What Are We Teaching Our Kids?

Now, as a mom, I find myself thinking about what messages I want my daughter to carry with her.

I can't prevent her from comparing herself to other girls. I can't make sure everyone likes her. I can't stop another kid from making a comment about her clothes, her body, or anything else.

I can't protect her from every insecurity. But I can help her develop better tools for navigating those experiences.

Because I think that's one of the hardest parts of parenting. We want to protect our kids from the things that hurt us. We want to make sure they never experience the shame, insecurity, or rejection we experienced.

But we can't actually do that.

Our kids are going to get hurt. They're going to compare themselves. They're going to wonder if they're good enough.

But maybe breaking the cycle isn't preventing those experiences but giving our kids different messages for how to react when they happen.

Instead of teaching them that being different is something to fix, we can teach them to get curious about themselves.

"What do you like?"

"What makes you feel good?"

"What feels like you?"

And part of parenting is letting them figure that out on their own. Because we're not raising children who will always need us to tell them who to be.

We're raising full human beings who will eventually decide that for themselves.

Being Yourself Doesn't Mean Being an Asshole

Now, there's an important distinction here.

"Be yourself" doesn't mean you get to be an asshole. We still need to teach our kids kindness, consideration, boundaries, empathy, and awareness of how their behavior affects other people. Being authentically yourself doesn't give you permission to hurt somebody else.

But wearing an outfit somebody else wouldn't choose?

Having unusual hair?

Liking a style your parents don't understand?

That's not harming anyone.

Someone feeling beautiful in a way you wouldn't personally feel beautiful doesn't take anything away from you.

In fact, I think there's something really wonderful we can practice here. We can learn to look at someone whose style is completely different from ours and think:

"Good for them."

Not, "I'd wear that." Not even, "I like that."

Just: "They clearly feel good in that. It's their thing, and I'm happy they found it."

There's a kind of compassion in that: The ability to experience joy or appreciation for someone else's joy even when what makes them happy isn't what would make you happy.

What if we taught our kids more of that?

Becoming More of Myself

One of the biggest things I've learned as an adult is that conformity never actually gave me the thing I thought it would.

I thought making myself smaller would make me safer.

Instead, the more I conformed, the less I felt like myself. The less brave I became. The less confidence I developed. The smaller my world became.

What has worked much better has been becoming more of myself, not less. The more authentically I show up in the world, the more I attract people who genuinely like who I am.

And yes, I also repel some people.

That's okay.

I'm not the right person for everyone.

Neither is my daughter.

Neither are you.

And neither are your kids.

Our job isn't to teach our children how to make absolutely everyone like them. That's an impossible assignment.

Maybe our job is to help them become secure enough in themselves that they can recognize the people who love them for who they actually are and let go of relationships that require them to disappear in order to belong.

So as you're helping your kids get ready for school this year, maybe don't just ask:

"What's everyone wearing?"

Ask:

"What makes you feel like you?"

Help them find clothes they feel good in. Let them experiment, change their minds, be a little weird.

And when another kid shows up wearing something neither you nor your child would ever dream of wearing, maybe that's an opportunity too.

We can teach them to think: "Good for them. They found something that makes them feel good."

Because I spent enough of my life trying to teach myself how to disappear.

I don't want to teach my daughter how to be smaller.

I want to teach her how to be herself.

And then I want to teach her how to find the people who fucking love her that way.