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This Jazz Singer Is Bringing Vintage Style to Life in Harlem

Dandy Wellington embraces fashion from the ’20s, ’30s, and ’40s — and confronts modern stereotypes.

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“People sometimes stare on the street at me,” says Dandy Wellington. The jazz singer, born and raised in New York City’s Harlem neighborhood, is referring to his natty three-piece suits, hats, wingtip shoes, bow ties, and other vintage items that he wears.

Wellington leads a jazz group called Dandy Wellington & His Band (check out the latest album, Winter Afternoon). His clothing incorporates styles from the so-called “Jazz Age” of the 1920s, as well as the 1930s and 1940s. The result is a tailored, quirky, personality-filled aesthetic with lots of unexpected touches — an Obama pin here, a paisley print there — all tailored to a tee.

“When people see a person of color dressing like this, they don’t really know what to do,” says Wellington. The ‘20s, ‘30s, and ‘40s, he says, “weren't great times for people of color.” And yet embracing a look that’s so unexpected is an empowering act.

It can also, unfortunately, be a protective maneuver.

“I’ve been very lucky that I’ve not had these interactions with law enforcement that many other black kids have, and some of that is my style,” he says. “A young black kid shouldn’t have to dress like me in order to just live their life.”

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