You undoubtedly know the look: Think loafers, button-up shirts, and navy blazers.

It basically started as sports clothes, says Trufelman.

It was kind of athleisure, Trufelman observes.

People of Color Wearing Country Club Style Clothing

Its the same mentality behind it.

But the Black folks do it differently.

So its not just about Can we look like Harvard at Howard?

A woman in a pink v neck sweater and tennis skirt

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Its also Can we look like Miles Davis?

Black people were in the country clubswe just werent members, he says.

Theres a lot of irony in it, and the irony is part of the joy, says Miller.

A model at the Fall 2024 Wales Bonner show

Giovanni Giannoni / WWD via Getty Images

Timberlands are work shoes, not dress shoes, she observes.

Its saying, I get this, but this is how it works in my context.

The marriage of preppy style and streetwear might seem at odds.

Andre 3000 and Big Boi in preppy clothes

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A suit is one thing, observes Penn.

But to have enough bread to be luxurious in a casual space?

Now your paper is up.

Serena Williams at the US Open in 2004

Clive Brunskill / Getty Images

Preppy fashion has managed to not only survive but thrive in the social media era.

American exceptionalism is first and foremost in how we present ourselves, as Penn says.

Low-key: Its all about cosplay in America.