Basquiat’s spiritual embodiment of cool

In mapping out Jean-Michel Basquiat’s sartorial style, particularly his spiritual embodiment of cool, something happened. I felt an upsurge of blood shooting north, followed, immediately, by a stillness so deep I almost burst into tears. Could this unseemly, perhaps inelegant feeling betray a too-long-suppressed, volatile wish to track the often-understudied history of cool’s African origins?

Mhhhm. Basquiat and, cool. Cool and Basquiat as its “New World” voodoo child. Mhhhm.

In fashion high stakes and its deeper underground bowels, why is cool so cold, so inaccessible, and hip so hot we always have to thatí cover under the shade? In style matters, in life itself or, perhaps, in matters of faith, I am haunted by cool and its implications. Its dialectic, its street, its languid flow on the catwalk, and uh, uh, its refusal to strike a pose. How cool has always stood on the outside of hip, but not only that. The recognition of how it also insists on standing on the outside of the thing that stands outside of hip. What renders it so elusive yet so effusive? Could it be because it derives its sorcery from its inherent contradictions?

You will recall how it has always rejected Hollywood while embracing some of its brightest, moodiest, never-maudlin lights — James Dean, Johnny Depp, Natalie Portman, that un-coolest cool thespian, Xavier Bardem, and the man whose first name only is enough to set 1 000 ships sailing, Denzel.

I wrestled with how Miles Davis had it and the “coolest” horn man of his era, John Coltrane, did not, at least not sartorially. How Charlie Parker — the self-taught, bebop outlier Basquiat made a fetish of eulogising — possessed too much of a kind of cool tethered to the weeping Afro-Atlantic winds ferrying African cargo in slave ships, primordial African spirit roots, and self-sacrifice that, ultimately, it did him in. I will not lie. The motivating idea was to revisit the uncomfortable, politically incorrect, zero- f*cks-to-give, outside-of-time, beyond-time power of cool to deface, defang, and vanquish hip forever.

At the base of my soul, I wished to extract the nasty power of cool to set off bad juju on all the pop-cultural industries that have used it in vain for much of the late 20th and early 21st centuries. That includes record labels, the advertising industry, fashion ateliers, architectural enterprises, and so forth — prior to the dawn of the Age of Irony and mass-prescribed behaviour with its saturation of pixelated 15 Warholian minutes substituting for culture.

Instead, I settled to filter it via a subject more specific, less ephemeral, less philosophical yet un-caged in its gay abandon, subjectivity, and biography — Basquiat. After years of studying cool and never quite getting it, I have arrived at these crossroads where to name is not only to shame but to also re-inscribe, erase, scratch, rename. Namely, that, without this beautiful, flesh-and-blood global African (Haitian and Puerto Rican ancestry) man-child, cool as we know it would have melted off in the late 1980s when jazz purists and Black conservatives lost the language to parse the resurrection of Davis to performance biz, complete with a hair weave, balloon pants, and purple sequins, just to see them commit mass cultural suicide.

Personally, my ultimate style icons revolve around this sextet: Miriam Makeba, Joan Didion, all the women in my family, especially Lillian Thuleleni Madondo, uhm… ahem, Steve McQueen in Papillon, and Davis. But what is style?

While subjective to its core, true style — as political as it is performative — implores us to gaze beyond our shadows and palettes. It taunts and compels us to shirk off our smallness, our coveted subjectivities. An impossible ask, for what is style if not an expression of unfiltered individualism? For close to three decades I have risked the hot tongue of many a lover, family member, and child for hoarding — there is no prettier phrase — boxes within which is a clutter of cuttings, stills, books, and film and video clips of artistic spirits. Of those boxes, the one marked “JMB” is one of the holy grails in all of my “rubbish”. Poring over hundreds of images spilling out of the pile, as well as, inevitably, the internet, I am drawn to an aspect of the man I feel is understudied.

I am drawn to his singular — some say “eccentric” and others refer to it, simply and urgently, as “call the police, there’s a strange Black man on the premises” — sartorial story. Trying to pin him down and failing is to reckon with why spending time in the stanky basement is, for fools like me, a recuperative moment in which trying to make sense of Basquiat’s meta-fictive biography is such a joyous kind of pastime. On all fours, dust sprinkled, I attempt, with no real possibility of denouement, to tease out scraggly strands of his visual speak, coded language, code switching, and decoding, to project sense where it was never intended. I try to extract at least the secrets of Basquiat’s inner style.

The process is not helped by his clashing, embedded narrative arcs, convoluted plots, dashes, commas here, and a refusal of exclamation marks, there. Here now. Gone tomorrow. As with the architectural style of Zaha Hadid; the punk impulses of Busi Mhlongo or her ultimate heir, Msaki; the black, blue, and bashed-into-the-skull Davis’s features; the mathematical genius of Ndebele art, tragically reduced to the work of one woman, Esther Mahlangu; Basquiat is, outside of hipster lore, dealt double death. No critical love for him, only gratuitous awe. Cursed are the beautiful for they will be ugly in our minds.

In the rare instances the subject is wrestled with, it is to reduce it to the artifice of hip. Rarely is it examined for its spiritual, nasty even, and exacting demands through which cool insists on being engaged with. His sartorial style, like his art, suffers from a kind of passionate indifference in the name of love. Everyone loves it and no one has the guts to reckon with the hate to which some of that love blinds us when we consider the man’s labour, and the jive he had to perform for the establishment that could not believe a boy so Black, so weird, carried such a lofty French name that he could also be an Afristocrat from the streets.

While Jean-Michel — shy, given to encrypted talk-in-tongues, nervous — has been all but reserved for exhibition catalogues’ end notes, Basquiat — stubborn urchin who played with paint, words, hue, sound, satire, strut, temporalities, brokenness, and impermanence — is now all but slave to the rhythm of shallow hip. For many within and beyond the wineclinking, Gucci’d-up, self-satirising, prêt-àporter world of art, Basquiat is not a person but a symbol. Unstable, impenetrable, misunderstood, young, dread-head with a penchant for white women.

Or how about this? A humanoid who once existed on the fringes of “normal” society. A Dambudzo Marechera doppelgänger. Perhaps a Jean Genet with baby-locks or bushman Afro. A shorthand for the urban bomber. For that’s his truest calling. Names. Labels. Tags. Lines. James Baldwin, yet another beautiful Black “boy”, might have put it more succinctly: Nobody knows his name. Jean-Michel’s style oscillated between New York’s mid-1980s nocturnal streets (part punk, part vagrant, part demimonde). Although his most enduring style is no-style, disavowal as opposed to fugitive, his loose, string-fastened-waist, striped pyjama suits anticipated the anti-chic chic of early 1990s Jean Paul Gaultier.

As with his art, music, and hacked, jagged, scratched but never erased calligraphy on canvas (poetry and words were his first love), the style philosophy of this man-child in Manhattan’s promised land, insofar as one existed, was marked not so much by a sensory load as layering. The layering was both deliberate and deconstructive. Part of his love for layering was his ability to de-clutter and pull out a solid, vintage, almost prohibitively classical austere look. It might be a Harlem-meets-Sophia-town colonial, bespoke zoot look popularised by figures such as Charlie Parker, Louis Armstrong, Miles Davis, Nat Nakasa, Zeke Mphahlele, members of the Spoilers gang, and Nelson Mandela at the 1956 Treason Trial.

Think of that black-and-white photo of Mandela and Moses Kotane bromancing in the sweltering Pretoria streets outside the Palace of Justice. Think of a dressed-down, respect-intact version of that visual shorthand. Sure, not all of it was new. He never claimed it was. Matter of fact, Basquiat would have been embarrassed by this essay. He never, almost ever, spoke about what he put on his body. The skinny, sometimes too roomy dinner jacket. The white, high-necked, collared shirt (known as a Mr B collar in reference to the man who made it pop on the jazz streets, Billy Eckstein). Skinny tie. Photo-lifted straight from the 1940s Teddy Boys but now, this being Basquiat’s 1980s, the trousers are straighter. He’d either add a biker jacket or dispense with the Mr B altogether in preference for a 1950s tight T, with lapels sticking out like a slaughtered beast.

He would accessorise the whole with a two-sizes-too-small vintage sporty hat beloved by B-Boys or Alexandra township golf caddies, and with that Black Mod remixed look, kill, kill all the looky-loos of the museum and gallery planet. I cannot think of anyone else who anticipated the icy, unflustered, minimalist power of what became Yohji Yamamoto’s incredibly demanding design ethos. Only one person in fashion anywhere on the planet evokes, for me, Basquiat’s enduring, inordinate yet ornate aesthetic ethos. That is Felipe Mazibuko, the freckled Black Queen of Joburg.

Sometimes I lapse into daydreaming. I imagine them on some city street, quite seedy, possibly an old red-light district, stealing looks at each other. When, per odd chance, their cold, cold, cool gazes collide in mid-air, they give each other an exaggerated evil eye. And you’d never know if, by that, they are putting on a mohair over passersby’s eyes, or not.

• Bongani Madondo is a photography theorist, poetry critic, and the author of several award-winning non-fiction books.

• From the October edition of Wanted, 2023.