Jean-Michel Basquiat’s Enduring Blend of High-Low Cool Endures in Art and Fashion

Jean-Michel Basquiat rocked the art world when he was barely 20, and his idiosyncratic sense of style also galvanized the world of men's fashion.

An art world darling at the tender age of 20, Jean-Michel Basquiat became as famous for his confidently cool style of mixing designer clothes with thrift store finds as he did for his powerful artwork that attracted the likes of Andy Warhol, Madonna, and power players of the art world of the '80s. With a life cut short at the age of 27 in 1988, Basquiat's art and personal style still wield heavy influence today, inspiring street style as well as Kanye and Jay Z.

Basquiat came up in a New York that was gritty, dangerous, and a hotbed of creative energy. New York in the '80s was a melting pot of vastly contrasting fashions that defined vastly contrasting lifestyles—power suits for the yuppies, Adidas and street wear for the rising hip hop scene, spikes and slashed clothing for the remaining punks, flash and splash for the exploding fame-obsessed downtown art scene. It was a time of unapologetic individuality, long before the internet transmitted information—and a concurrent homogenization of style—within seconds.

Basquiat's style came from the same philosophy as his paintings where he mixed and contrasted ideas like poverty and wealth, segregation and integration, even figuration and abstraction, all of which he referred to as "suggestive dichotomies" in his artwork. These conflicting notions were unified by his energetic and sloppy brushstrokes, whose vibrant intensity captured the attention of art dealers everywhere.

epa european pressphoto agency b.v. / Alamy Stock Photo

His esthetic in clothing was much the same. With the beauty of contrast in mind, Basquiat pioneered an easy, confident mix of uptown and downtown, combining street wear with formal wear while looking undeniably cool. Topped with his signature lop-sided pigtails, he could be found in suit coats, bold prints, slouchy jackets, and skinny ties. Even after he hit the big time in 1981, his high-low mesh continued to flourish, but by then he was playing with designer suits instead of thrift store finds. He favored Armani, Issey Miyake, and Comme de Garcons, the latter asking him to walk in their spring/summer presentation show in 1987.

Being the quintessential Downtown artist, Basquiat treated his Armani threads like painter's smocks, wearing them in the studio all day, then going to the clubs in the paint-smattered suits all night. Several portraits of Basquiat from that time show the artist in elegant suits while barefoot, exuding a bit of indifference and a bit of narcissism, demanding the viewer accept this incomplete look as his own. His disregard for the preciousness of designer clothes made him all the more iconic—the designer labels certainly did not define him. Instead, expensive designer clothing simply became incorporated into his existing style, used merely as a cog in his complete look.

Everett Collection Inc / Alamy Stock Photo

Today chain stores and glass towers have displaced the once thriving Downtown New York art scene, while Basquiat himself long ago became part of the 27 Club from a heroin overdose. But even though millennial New York is a very different place, Basquiat's influence can still be felt, even in the current Disneyland-like version of his city, both in art (one of his works went for more than $57 million at Christie's earlier this year) and in fashion.

True, some of this "influence" is just corporate appropriation: Many labels have licensed his art works for hats, shirts, shoes, pins, bags, you name it. But far more important, his power clashing of high and low and his way of meshing texture and color have become the norm for modern men's fashions. You can see his influence just by walking down any New York street—from pairing T-shirts with blazers to bringing sneakers into high fashion by wearing them with suits, contributing to the profound societal sneaker obsession that started in the late '80s. Basquiat's look—once avant-garde and iconically his own—paved the way for today's classically cool mash-up style.

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