Some musicians just don’t dress like you’d expect them to. Who could guess that Charlie Watts of the Rolling Stones looks like a Saville Row tailor when Keith Richards is always in Rasta pirate cosplay? Or that the king of neo-folk music, Sufjan Stevens, would eschew generic staples like Aran sweaters and chambray shirts for a technicoloured wardrobe that’ll have you mistaking him for an EDM DJ?
Then there are musicians who don’t just dress like you think they should, but whose clothing perfectly matches the aesthetic of their music, as though their wardrobes were part and parcel of some grand creative vision. Such an artist is Miles Davis. His clothing choices matched his music note for boundary-pushing note, from the sleek, laid-back cool of his early years all the way through the authored chaos of his late career.
Way back when he was starting out, however, Miles was too broke to be an iconoclast. When he played on stage with bandleaders like Charlie Parker and Count Basie, Davis pulled together what little money he had to buy himself second-hand Brooks Brothers suits. Hoping to look as dapper as a cat like Dexter Gordon, he saved up for an oversized grey suit with big shoulders that cost him $47. In his words, these early suits had him looking ‘clean as a broke-dick dog’.
When he came into his own as a solo artist in the 1950s, however, Davis eschewed the bold stripes, wide lapels, and broad shoulders of the jazzmen of the generation prior in favour of a simple, Ivy-inspired look.
At that time he had been playing university campuses around the U.S. and took inspiration from the clothes he saw college kids wearing. With the help of Charlie Davidson at the Andover Shop in Cambridge’s Harvard Square, Davis traded in his zoot suits for tweed and madras jackets, all cut with narrower lapels and tailored to accommodate his hunched trumpet playing style. He bought chinos, button-downs, knit- and rep ties, and Bass Weejun loafers to top it all off.
With this new wardrobe, Davis took on the look of the hallowed, historically white halls of the academic establishment and brought it to African American communities and the world at large. A great example of this can be found in perhaps his most iconic outfit from this period, which he wore on the cover of 1958’s Milestones. The record features Davis wearing dark slacks, a pinky ring, and a beautiful, sea green button-down shirt. It was enough to have hipsters the world over — including the aforementioned Mr Watts before he joined the Stones — scrambling to find a similar shirt. As Alfred Tong points out in the Guardian: ‘Back then, jazz album covers (especially those by artists such as the Modern Jazz Quartet, Chet Baker and Miles Davis) doubled up as fashion plates, communicating a new style and attitude to the first generation of London mods.’
1950s-era Miles gelled well with the aesthetic of his style icons Fred Astaire, Cary Grant, and the Duke of Windsor. ‘I created a kind of hip, quasi-black English look: Brooks Brothers suits, butcher boy shoes, high top pants, shirts with high tab collars that were so stiff with starch I could hardly move my neck,” Davis wrote in his autobiography. It allowed him to look as sharp as possible at a time when black artists struggled to get recognition as more than just entertainers. As the sax player and composer Wayne Shorter put it: ‘He always dressed well, always in tune with fine things, and he didn’t see any reason why fine things should be denied to anyone.’
Even at this point, when Davis’ dress sense was at its most restrained, there were already hints of what was to come: the bright sparkle of a flashy ring, a watch with an elaborate bund strap, a kerchief worn under the collar of his button-downs. Davis always had adventurous tastes, which he said he’d inherited from his mother. ‘She had mink coats, diamonds,’ he wrote. ‘She was a very glamorous woman who was into all kinds of hats and things, and all my mother’s friends seemed just as glamorous to me as she was. She always dressed to kill. I got my looks from my mother and also my love of clothes and sense of style.’
Things really began to kick off when the ’60s and ’70s rolled around. By 1960 Davis had already traded in his sack suits for slim-cut European tailoring and handmade doeskin loafers. Later on, his friendship with fellow iconoclast Jimi Hendrix would influence his music and style alike. As Davis music became ever more avant-garde, his wardrobe followed suit, reflecting the changing times and his ever-expanding sensibilities. He began wearing Indian shirts, dashikis, and suede trousers by the young African-American designer Stephen Burrows. He grew out his hair, bought shoes with chunky heels, and sported the bevvy of bug-eyed sunglasses that would become his late-life signature.
One of his outré outfits even saved his life. In 1969 he survived a drive-by shooting on his Ferrari while he had on a loose-fitting leather suit. As he tells it: ‘If it hadn’t been for that leather jacket and the fact they shot through the door of a well-built Ferrari, I would have been dead.’
Even in his final years, Davis remained on the cutting edge. In the ’80s he discovered Japanese designers like Issey Miyake and Kohshin Satoh. He wore the latter during a White House visit in 1984 and also modelled Satoh’s clothes alongside Andy Warhol in 1987.
Before his death in 1991 Miles Davis had done and worn it all. In this sense, he was the ideal dresser. He took equal inspiration from the past and the present, he knew what he liked but wasn’t afraid to experiment, and he moved with the times while maintaining a distinctly individual look. His refined tastes and liberal sensibilities meant that he always had on (as Down Beat magazine put it in 1960) ‘what the well-dressed man will wear next year’. He was, in music as in fashion, enviably and inevitably, always miles ahead.
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