Ever wonder why you wear what you wear? It might seem like a simple choice—jeans or sweats, boots or sneakers—but behind every outfit is a weird, tangled mess of history, culture, insecurity, and confidence. In this episode, you’ll take a walk through some decades of fashion—from buffalo fur for survival to kids wearing pajama pants in public.

We start where clothing really began: not on the catwalk, but in cold weather. You wore what you needed to stay alive. There was no "style"—just fur from the predator to throw on your back. But over time, things shifted. Clothing became about power, wealth, and status. Kings, queens, and the upper crust dressed in elaborate and uncomfortable outfits—to prove they could afford it and you couldn't.

For decades, fashion stayed in its lane: suits and hats for white-collar workers, overalls and work shirts for blue-collar folks. Women’s clothing followed strict, conservative rules. Then - the 1950s and 60s showed up. With the rise of TV and youth culture, fashion stopped being about rules and started being about being different.

Some trends got weirder, louder, and more experimental—from Kriss Kross wearing pants backwards to Michael Jackson putting his underwear on the outside. In hindsight, it all seems ridiculous—but it made sense at the time, right?

This episode digs into how we use fashion to distance ourselves from the generations before us. As a kid or teen, you could wear the wildest thing and pull it off—just because you were young. This energy is basically magic. But somewhere along the line, usually in your 30s or 40s, you stop trying so hard. You wear what feels good. You stop caring what anyone else thinks—and there’s a real freedom in that.

But it’s not all peace and pajama pants. We talk about the insecurity of youth, the slow build of adult confidence, and the very real possibility that something you love wearing today might be laughable in ten or twenty years. And that’s okay.

Because fashion has never made complete sense. It’s not supposed to. It’s about identity, energy, self-expression—and sometimes just putting something on that makes your wife say “goddamn.” Whether it’s three little buttons on a shirt or the weird flannel pants everyone’s suddenly wearing to school, you wear the things that make you feel like you.

So wear whatever you want and don't let anyone tell you it's not cool. You will be your biggest critic in the future anyway-

Opening song “Chiptune Fighter" written by SCOREWIZARDS.

All production by Cody Maxwell.

Opening graphic assets by motionstate.

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