Dressing for Herself: What Sending My Daughter to Middle School Is Teaching Me About Breaking Old Cycles

My daughter, Olivia, is going into middle school.

And apparently, sending your daughter to middle school has a funny way of sending you right back to your own middle school years.

As a mom and a therapist, I find myself thinking about this constantly:

How do I change some of the things that hurt me growing up so that my daughter gets a different experience?

I know I can't prevent every painful experience. I can't make sure she's always included. I can't stop another kid from saying something mean. I can't prevent puberty, insecurity, comparison, friendship drama, or all the other things that seem to suddenly get turned up to full volume in middle school.

But maybe I can change some of the messages she takes with her.

And today, of all things, I started thinking about clothes.

What Are Middle School Girls Even Wearing?

With school approaching, I went window shopping. I wasn't really trying to buy much yet. I wanted to look around, see what was in the stores, and yes, look at girls around Olivia's age.

What are they wearing?

What are the styles right now?

What are some good basics?

What actually seems comfortable and cute for a middle school kid?

And while I was looking, I realized something about the way I used to shop at her age. I would look at the other girls and try to mimic them. If something looked cute on another girl, I wanted that exact outfit.

The problem was that I didn't have her body. I've always had a bigger body. I'm tall. I wasn't built like the petite girls I was comparing myself to.

So I would take the clothes that looked adorable on someone else, put them on my body, look in the mirror...

And they didn't look the same.

The conclusion I drew wasn't: "Maybe this particular cut isn't right for my body."

The conclusion middle school me reached was: "Something is wrong with my body."

And shame crept in.

I Want to Teach Her Something Different

It took me years to learn something I wish I had understood in middle school:

You don't have to dress someone else's body. You get to dress yours.

As I got older, I started watching makeover shows and learning about clothing differently. Shows like Queer Eye for the Straight Guy and all those fashion shows that taught people how to dress for different shapes, coloring, proportions, and personalities fascinated me.

The message was completely different from the one I'd internalized as a kid.

You didn't have to change your body to become beautiful. You could learn how to dress the body you already had.

Whether your body type is pear, apple, hourglass, tall, short, curvy, or petite.

Whatever.

Then you could pay attention to shape, color, fit, fabric, proportion.

And eventually, I learned to dress for me.

That's something I want to pass on to Olivia.

Of course you can look at other girls for inspiration. That's part of fashion. That's part of being a teenager. But inspiration doesn't have to mean imitation.

We can look at what's popular and then ask:

What looks good on YOU?

I don't particularly care what number is printed on the tag. I care about what happens when you put it on.

Do you walk out of the dressing room feeling good?

Do you feel comfortable?

Do you stand a little taller?

Do you feel like yourself?

Or do you spend the entire time pulling the shirt down, tugging the pants up, adjusting something, hiding something, or worrying about how you look? Because those feelings matter more to me than whether you're wearing the same thing as everybody else.

And Then Comes the Hard Part of Parenting

Even as I think about how I want to teach her this, I realize something else:

I can't control all of it.

I already see her comparing herself to other girls. I see the other girls comparing themselves to one another. There's something about this age where suddenly everybody becomes much more aware of everybody else.

Do they like me?

Am I pretty?

Do I fit in?

Am I wearing the right thing?

What do people think of me?

Maybe it's puberty. Maybe it's development. Maybe it's simply part of figuring out who you are.

And as her mom, I can't take that process away from her. I can only try to give her some healthier tools while she goes through it.

Maybe that's part of breaking generational cycles, too.

Sometimes I think we imagine healing the next generation means making sure our kids never experience the things we experienced. But we can't do that.

Our kids are still going to get hurt.

They're still going to compare themselves.

They're still going to have insecurities.

They're still going to have awkward middle school moments.

They're still going to have to figure themselves out.

Maybe breaking the cycle isn't giving our kids a life without pain. Maybe it's giving them different tools and different messages when the pain comes.

To the Other Moms Doing Back-to-School Shopping

So, as we moms head into tax-free weekend, wander through clothing racks, buy school supplies, and prepare our kids for another school year, maybe we can give ourselves a little grace, too.

Some of us are sending kids to kindergarten.

Some are sending them to middle school.

Some are watching teenagers walk into high school.

And sometimes these milestones bring up our own memories right alongside theirs.

We're trying to figure out what to repeat, what to change, what to teach, what to let go of, and when to simply stand nearby while our kids figure something out for themselves.

We're not going to get all of it right.

But we're trying.

And those little changes matter.

Maybe it's as simple as standing in a dressing room and teaching our daughters:

You don't have to make your body fit the clothes. Let's find clothes that fit you.

You can notice what everyone else is wearing. Be inspired by it. Experiment.

But ultimately?

Dress for yourself.

Then maybe, little by little, that's how we help the next generation carry a little less shame than we did.