Not just a jazz genius, Miles Davis was also a sartorial chameleon, easily carrying off the Ivy League look and slim-cut European suits with ass-kicking charm.
by christian chensvold re-photography stephen landau
ate in his career, Miles davis stopped playing the stark, haunting ballads that had been one of his trademarks. he loved them too much, he said, to go on playing them when they were no longer in style. Throughout his four decades in jazz, in which he was at the forefront of every major innovation, Miles davis always shunned the stale and the hackneyed — what he called “warmed-over turkey”.
Shot onstage in 1959 (right), we move Miles ahead (this pic) with: Camel double-breasted wool suit, Ermenegildo Zegna; Striped cotton shirt and slim silk tie, both Brooks Brothers; Silk printed pocket square, Etro; Watch, Tudor.
This artistic integrity, this determination to be unpredictable, to stand for the new and to take risks, is key to understanding davis’ chameleon-like role as a style icon. Under ‘The Warlord of the Weejuns’, the headline for the liner notes for a 1965 greatest hits collection, celebrated Esquire writer George Frazier called davis “a truly well-dressed man”, but someone the average man would be foolish to emulate. “i’m not advocating that all men aspire to dress like davis,” Frazier writes. “That would be unrealistic, for it is this man’s particular charm that he is unique.” in fact, Miles davis should be every man’s sartorial role model, for he achieved what few others do: epitomising changing eras while crafting an individual style. davis was no stick-in-the-mud wedded to a lifelong look, but neither was he a malleable fashion follower taking orders from the marketplace. he was perennially a man of his times yet ahead of the pack, wearing, as DownBeat magazine wrote in 1960, “what the well-dressed man will wear next year”. it wasn’t always that way. When he joined the st. louis musicians’ union at age 16, he was too poor to be ahead of the curve, and had to settle for secondhand Brooks Brothers suits from the local pawn shop. Miles thought he looked sharp (“clean as a broke-dick dog” was his exact expression), but hipper cats like dexter Gordon didn’t agree. Miles writes in his autobiography: “dexter used to be super hip and dapper, with those big-shouldered suits everybody was wearing in those days . i was wearing my three-piece Brooks Brothers suits that i thought were super hip, too. But dexter didn’t think my dress style was all that hip. [i said to him] ‘Why, dexter, these some bad suits i’m wearing. i paid a lot of money for this s***.’ [dexter replied] ‘Miles, that ain’t it, ’cause the s*** ain’t hip. see, it ain’t got nothing to do with money; it’s got something to do with hipness.’ “so i saved up 47 dollars and bought me a grey, big-shouldered suit that looked like it was too big for me.” in 1955, davis signed his first major-label deal, with Columbia Records, and just as the silhouette of his suits changed from broad to natural shoulders, so too did Miles begin setting styles rather than following them. “in the mid-’50s, Miles took to the ivy league look in fashion,” writes jazz historian John szwed, “having his clothes made at the epicentre of preppy fashion, the Andover shop in Cambridge’s harvard square, where tailor Charlie davidson dressed him in jackets of english tweed or madras with narrow lapels and natural shoulder, woollen or chino trousers, broadcloth shirts with buttondown collars, thin knit or rep ties, and Bass Weejun loafers. it was a
Miles was perennially a man of his times yet ahead of the pack, wearing, as DownBeat magazine wrote in 1960, “what the well-dressed man will wear next year”.
Miles is pictured below recording in 1959. The Rake’s rebirth of the cool look (above) comprises: Grey singlebreasted wool suit, Alfred Dunhill; White cotton shirt, Charvet (Property of The Rake); Black silk tie, Alfred Dunhill (via Aston Blake); Sterling silver cufflinks, Bulgari. Miles smiles at fellow legend Dizzy Gillespie (above left) in 1958. Our remastered ensemble (far left) features: Black single-breasted suit, Giorgio Armani; Striped cotton shirt, Thomas Pink.
“For Miles, the music is the central component of a larger aesthetic project that includes fashion, painting, boxing and self-creation.”
original photos: getty images art direction: darius lee styling: charlene lee styling assistant: anjali d
Miles is kind of blue in a New York studio circa 1959 (opposite page). Our update (this pic) includes: Grey light wool sweater, Burberry London; Cream treated cotton trousers, Brooks Brothers; Black low-cut leather buckle boots, Louis Vuitton; Rust silk printed scarf, Hermès.
look that redefined cool and shook those who thought they were in the know.” it was during this period — the time of such groundbreaking albums as ’Round About Midnight, Miles Ahead and Porgy and Bess — that davis became the iconic figure he’s remembered as today. here was the “evil genius of jazz” hunched over his trumpet, his jackets cut specifically for his slouchy playing posture, his back to the audience, never once addressing the crowd, and frequently leaving the stage while bandmates took their solos. But Miles’ arrogance and aloofness only added to his allure. As Farah Jasmine Griffin and salim Washington note in their recent book Clawing at the Limits of Cool, while Miles’ coolness and glamour were rooted primarily in his music, “they were more than bolstered by his physical beauty and sartorial elegance, his complicated relationships with beautiful women, and most of all, his take-no-shit attitude”. This attitude could elevate the most commonplace clothing items to artistic expressions in their own right. Take the simple white
button-down shirt Miles was photographed wearing, sleeves rolled up, during the 1959 Kind of Blue sessions. “The shirt is tucked neatly into his pants,” write Griffin and Washington. “he is tight and fit, in full control, in top form... an aesthetic statement.” Though he admired legendary dressers like Fred Astaire, Cary Grant and the duke of Windsor, Miles’ true role model was the boxer Jack Johnson, whose fine clothes, fancy cars and beautiful women seemed to unify his lifestyle into a coherent statement. “For Miles,” write Griffin and Washington, “the music is the central component of a larger aesthetic project that includes fashion, painting, boxing and self-creation.” By 1960, Miles was a GQ fashion plate and on Esquire’s bestdressed list. ever ahead of the pack, he’d already moved on to slimcut european suits. Press releases for upcoming concerts detailed the sartorial as well as musical programme. A 1961 press release for the Randall’s island Jazz Festival outlined Miles’ onstage and backstage outfits, which included a one-button beige pongee suit, a pink seersucker jacket, and handmade doeskin loafers. What a man loves often destroys him — or at least drives him to distraction. in a famous 1971 photo by Anthony Barboza, davis stands in front of a walk-in closet overflowing with scarves, belts and boots, an avalanche of paralysing options. in The DownBeat Miles Davis Reader, Keith Jarrett remembers visiting Miles at his apartment: “he was in his room with all his clothes, and he was looking at this wall-to-wall closet and wall-towall shoes. And he’d come out of his room with one thing on, and then he’d go back in, and then he’d come out of his room and he’d have something else on.” When Miles finally left the apartment, he scoffed at his life, curses, muttering, “Bitches and clothes, bitches and clothes!” he’d finally decided what to wear — if only for a day.