Models wearing Sean John's new capsule collection featuring Basquiat.

Basquiat and Sean John may not seem like the most natural pairing, but commerce isn’t known to defer to art.

As part of its ongoing celebration of 20 years in business, the brand, founded by Sean “Puffy” Combs and led nearly all the while by president Jeff Tweedy, launched a capsule collection of nine pieces featuring three works by the late Jean-Michel Basquiat, who has become something of an artsy touchstone for hipsters of all ages.

“We wanted to look at, how do we cultivate a world of fashion, pop culture and entertainment, keep all of that together,” Tweedy said in a relatively quiet corner of a crowded party at a Chelsea art gallery toasting the capsule’s launch. “If you look at who Jean-Michel Basquiat is, he is pop culture, he is that and his art is amazing and we just felt that we could really pay homage to him and to our collections and do a wonderful collaboration.”

Basquiat started out as little more than a graffiti artist on the streets of Seventies New York, where he was born and died of a drug overdose in 1988, but not before reaching a celebrity status rarely seen in the art world, and not before Tweedy says he saw on the street one of his most notorious early tags: SAMO.

“You know what that stands for? Same ol’ shit,” Tweedy said. “He was making a statement of the time and it’s still relevant to where we’re at today.”

While Tweedy said he’s long been a fan of Basquiat and that Combs [who was not at the launch party] owns two of his works, the capsule sounds like it’s the beginning of a larger focus on collaborations for Sean John going forward. There’s at least one coming up with Bloomingdale’s, which was the first store to carry the brand, and New York’s Fashion Institute of Technology will have an exhibit this fall of collections past, Tweedy said.

With the still-growing popularity of streetwear, and within that scene an ironic nostalgia for vintage pieces from brands that, often in spite of their best efforts, became “urban” favorites, Sean John seems eager to tap into a moment of becoming more widely relevant.

And Tweedy is aware there’s an opportunity. For the anniversary, Sean John is planning to rerelease its “iconic pieces” with the velour tracksuit, which hasn’t been available for at least 12 years, coming out “front and center,” according to Tweedy.

The brand is also looking to break out internationally this year. There are talks revolving around India, although Tweedy was thrown by the absence of billboard marketing. But China is likely to be first, followed by South America and the U.K. This all makes sense given the company’s relatively new financial partner, Hong Kong-based Global Brands Group.

But the Basquiat collaboration did raise some eyebrows. A dapper partygoer dressed in a slim gray plaid suit and a black turtleneck was taking in the pieces being shown on five male models that stood on white blocks near the entrance of the gallery said the coolest part of the looks were hand-painted Doc Martens, which are not for sale. The rest of the pieces, including a paint splattered denim jacket and an almost preppy black pullover featuring Basquiat’s “Pez Dispenser” and simple cotton shirts with “Basquiat,” he felt were a definite departure for Sean John.  

“People are here because of Sean John, Sean Combs,” the attendee said gesturing out to the crowded space. “This looks like something that should go into Urban Outfitters. I wonder how it’s going to work.”  

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