I Really Thought the Right Shoes Would Help Me Fit

Why fitting in isn’t the same as feeling like yourself

Originally published on Substack April 14, 2026

I don’t know about you, but I desperately wanted to belong in school. I was convinced that if I just had the right clothes and the right shoes, that would be my way in.

In fifth grade, my entire class of 15 kids was sent from our small country village school to the “big city” (population 26,000) to join another elementary school. There were three classes of 30 students each. I had never been anywhere close to that many kids my age. I was a country mouse among city mice.

In my head, I was doomed from the start. My clothes didn’t look like what the other girls wore. I felt like I was missing something.

I wore mostly hand-me-downs, and I definitely didn’t have the right sneakers. Every other girl wore what we called “Baldies,” which were actually low-top blue Chuck Taylors. I wanted them so badly, but I had already gotten my yearly allotment of shoes: one pair of dress shoes and one pair of white Keds.

I needed those white Keds because my one extracurricular was baton twirling, and they were required for competitions.

So I made a deal with my mother. If those Keds wore out, I could replace them with Baldies. But they had to be white, not blue.

It was not a good compromise.

Those white sneakers made me stand out even more as the girl who didn’t quite fit in.

I remember thinking the problem was obvious. If I could just get closer to what everyone else was wearing, everything would fall into place.

I don’t think that instinct ever fully leaves us.

It finds more subtle ways to show up, often through our insecurities.

Am I doing this right?

Does this look like me, or like I tried too hard?

Why does this work on her but not on me?

I’ve been paying attention to the fashion influencers who seem to be the most popular right now. They are good writers. They seem sincere. They are clearly knowledgeable.

But when I step back and look at the clothes, they are all remarkably similar.

Wide-leg or straight-leg jeans.

T-shirts or button-down shirts.

Oversized sweaters.

Long coats.

Slouchy handbags.

Simple flats or low-rise vintage sneakers.

And a very controlled palette of black, navy, ivory, gray, and camel.

There is nothing inherently wrong with any of it. In fact, it all looks comfortable and pulled together.

But it is also very repetitive.

As a professional color analyst, and someone whose favorite Christmas gift as a child was a box of 64 Crayola crayons with the sharpener built into the back, it feels unnecessarily limiting.

There is an entire world of color available to us, and it’s very hard to find yourself when you’ve already narrowed the options.

Because somewhere along the way, “this works” has quietly turned into “this is what you should wear.”

And those are not the same thing.

I remember thinking the answer was just getting closer to what everyone else had. But those white sneakers didn’t make me feel like I fit in. They only made me more aware that I didn’t.

And I wonder if, as adults, we’re still doing a version of the same thing.

Adopting the silhouettes.

Buying into the palette.

Following the formula.

And still, somehow, feeling slightly off.

Because the issue was never just the clothes.

It was whether they felt like us.

We get to decide what we want our clothes to say about us. Our goals. Our dreams. Our unique selves.

So instead of asking, “Is this what people are wearing?” a better place to start might be:

What do I reach for without thinking?

What do I feel most like myself in, even if it’s not what’s being promoted?

What colors make my face come alive instead of fade into the background?

That’s where your real starting point is.

Not in the uniform.

But in the pieces that already feel like home to you.

From there, you can refine. You can elevate. You can build.

But you’re building from something that’s yours, not something you’re trying to approximate.

Because “fitting in” and “feeling like yourself” are not the same thing.

And most of us already know which one we actually want.

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