The Feeling of Expensive

Money is weird about this bag

Fashion is weird.

And I love it.

Do you remember the Stephen Sprouse / Marc Jacobs Louis Vuitton graffiti bag?

In my world at the time—trying, somewhat seriously, to be the best-dressed American student at the LSE—it felt like a statement: we’re here.

Not because it’s expensive. Louis Vuitton has always been expensive. What was different is how the 2001 graffiti bag changed the feeling of that expense.

Luxury usually creates two barriers. The first is price. The second is behavior. Even if you can afford it, there’s still a question: can you live with it the right way? Or are you an impostor?

You don’t put it on the floor. You wrap it back in its cloth. You put it back in its heavy box. You’re aware of it in a way that makes it hard to forget what it costs.

It’s not just expensive. It asks you to behave like something expensive happened.

“I can afford this.”

“I might still do this wrong.”

You’re not just carrying it. You’re managing it.

And the truth is, people with real money don’t behave like that. They don’t flinch. They wear the expensive shoes like they’re cheap. The object isn’t fragile to them, because their position isn’t fragile.

The graffiti bag said: hold up, wait a minute.

It took maybe the most protected symbol of luxury and treated it like something disposable. The street is the design. The monogram is the canvas.

And that softens the anxiety. It invites you to live with it, not preserve it. The point is to actually enjoy it. It’s fun.

That’s what makes the bag interesting.

Louis Vuitton let in a visual language it didn’t invent and didn’t fully control. The graffiti isn’t cleaned up. It still feels fast, slightly careless—like it came from somewhere else.

So instead of saying “this is fashion,” it feels like it’s saying: we see what’s becoming fashion.

It felt inclusive. Not in a marketing sense, but in a control sense. Luxury loosened its grip—on taste and on behavior—just enough to let something in.

And that’s what holds value.

Not just rarity. Not just design. But the fact that, for a moment, the system relaxed.

And you could feel it.

It feels, right now, like a good time for leaders to remember how to do that.

Feels worth acknowledging where that started.

Marc Jacobs knew.

Money is weird.

Fun should be for all.