You Think You're Buying Shoes

I try to be very intentional about what I spend.

I think the key is being proactive instead of reactive.

Over time I’ve built a kind of uniform. Right now it’s brown Sperry Top-Siders, black Lululemon ABC pants, and a black crewneck. It’s simple, me, and most importantly it keeps me from buying clothes impulsively, which I’m very good at.

The uniform solves a problem.

Sometimes I see clothes that look great on other people and think they might look great on me too. The uniform helps me remember those are two different things.

But then I saw these shoes.

Supreme / Nike SB Air Max 2 CB ‘94.

And somehow the uniform didn’t stand a chance.

I’ve been obsessed with the mid-90s lately. We’re watching the JFK Jr. love story show, which lives in that moment. Something about the era feels nice right now. Simpler maybe. Or maybe just far enough away to feel romantic.

Wait, someone just hit me on my pager. 823.

And when I saw those shoes something else came back to me.

I remembered a kid I didn’t know wearing the original mid-tops when I was taking the SATs. I still remember that moment on the UC Berkeley campus more than the room where we took the test.

I would have given ten points off my score to have those shoes.

So when I saw them again, thirty years later, I bought them.

Two hundred dollars. Immediately. I bought them before I could stop myself.

Here’s the strange part though.

The jury is still out on whether this was a good $200 or a bad $200.

Right now it feels a little ridiculous.

I can’t wear them to work. And I won’t resell them because I’ve never resold a pair of shoes in my life.

But that’s a weird thing about money.

Sometimes you spend $200 on dinner, enjoy it, and never think about it again.

And sometimes you spend $200 on something you didn’t need at all, but it reconnects you with a moment in your life.

You think you’re buying shoes.

But maybe you’re buying a memory. Maybe you're buying being seen. Maybe both.

I wonder if I could have just enjoyed that memory without buying the shoes.

I'll tell you one thing… I'm gonna catch a few people off guard with them.

And that makes me smile. That makes me feel seen. And it helps me remember a time when I couldn't just buy sneakers.

And I like that.

---

A Few Behavioral Finance Ideas Behind This

Choice Architecture

We can design simple habits — like a clothing “uniform” — to make everyday decisions easier.

Impulse Buying

Sometimes emotion moves faster than reflection, especially when something suddenly feels meaningful.

Nostalgia Bias

Memories from earlier in life can make certain objects feel more valuable than they objectively are.

Identity Signaling

What we buy often says something about who we are — or who we remember being.

Emotional Utility

Not every purchase is about practical value. Sometimes the return is a feeling, a memory, or being seen.