Anna Wintour

Luxury doesn't mix with mass market.

It's like putting a Ferrari engine in a Toyota.

It violates the hierarchy that lets luxury charge luxury prices.

Anna broke that law on purpose.

She understood something the industry didn't.

People don't dress in just Prada or just Gap.

They mix.

She was documenting reality while everyone else was protecting mythology.

This is how disruption often works.

You don't invent new behavior.

You legitimize behavior that already exists.

But the Madonna cover reveals her deeper insight.

A businessman on a plane tells Anna he loves Vogue because it's so elegant, so classic.

Katharine Hepburn, Grace Kelly.

It would never be Madonna.

Most editors would take this as market research.

Our readers want elegance, not controversy.

Anna heard it differently.

If everyone agrees Vogue would never do something, that's exactly what would get attention.

And I would go on to say the fact that that very nice man that I sat next to on the plane thought that it would be completely wrong to put Madonna on the cover and completely out of keeping with the tradition of Vogue being this very classically correct publication pushed me to break the rules and had people talking about us in a way that was culturally relevant, important, and controversial, all of which you need to do from time to time.