This was originally written for a fashion company. It is here because on November 13th there is a playback of Kind of Blue using the UHQR (Ultra High Quality Record) vinyl version that plays at 45rm (and consists of two discs) in a North London pub. Details at the end of the article. Photographs are from the official Miles Davis site (https://www.milesdavis.com/gallery/miles-davis-photos/)

Miles Davis, as well as being one of the most influential jazz musicians in the world, was also one of the most stylish. Looking good was as much an obsession as the sound of his trumpet. “For me, music and life are all about style…. you’ve got to have style in whatever you do – writing, music, painting, fashion, boxing, anything.”

Herbie Hancock remembers: “Miles was always the hippest guy around. The way he moved, the way he walked, the way he stood when he played, what came out of his horn, and the cars he drove [Ferraris and Lamborghinis], all of that was stylish. That was part of his persona.” Saxophonist Wayne Shorter once told the New York Times: “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. He grew up  that way.”

       Davis himself confirmed Shorter’s assertion that his embracing of the high life had its roots in his upbringing in a middle-class, aspirational family in East St Louis. “[My mother] had mink coats, diamonds,” Miles wrote in his autobiography. “She was a very glamorous woman who was into all kinds of hats and things. She always dressed to kill. I got my looks from my mother and also my love of clothes and sense of style.”

       Still, he needed a little fashion advice when he went out into the world to earn a living as a musician. Future saxophone great Dexter Gordon, always known as a dapper dresser, took him aside and told him to ditch the over-sized suits he was wearing. Miles protested that he had paid a lot of money for them. “It ain’t about money,” replied Gordon. “It’s about hipness.”

      Miles responded positively to the criticism, not always a given (one of his favourite brush-off phrases – “So what?” -provided the name of a pivotal tune on Kind of Blue, his ground-breaking, best-selling modal album). “So, I created a kind of hip, quasi-black English look: Brooks Brothers suits, butcher boy shoes, high-top pants, shirts with high tab collars.” In the mid-Fifties he moved from Brooks Brothers to frequenting the Andover Shop in Cambridge’s Harvard Square, where tailor Charlie Davidson dressed him in jackets of English tweed with narrow lapels and natural shoulders, woollen trousers, broadcloth shirts with button-down collars, thin knit ties and Bass Weejun loafers. As anthropologist and jazz scholar John Szwed explains: “It was a look that redefined cool.”

       Like his music, which in the space of ten years moved from bop to post-bop to orchestral “third stream” to modal and back to chordal, Miles’s fashion sense was in constant flux. Downbeat magazine once said Miles wore “what the well-dressed man will be wearing next year”. Unlike other jazzers, he regularly featured high in both the Esquire and GQ best-dressed men lists. Why?

  In their book Clawing at the Limits of Cool, Farah Jasmine Griffin and Salim Washington argue that (as Dexter had advised him) it was as much how he wore his clothes as his choices that made Miles the fashion plate he became: “They were more than bolstered by his physical beauty and sartorial elegance, his complicated relationships with beautiful women, and most of all, his don’t give a [damn] attitude.”

        This, they suggest, was a man who could take a simple, well made, white button-down shirt with the sleeves pushed back and elevate it new heights of sartorial semiotics.  “The shirt is tucked neatly into his pants,” they write of his appearance in the Kind of Blue sessions, “He is tight and fit, in full control, in top form… [it is] an aesthetic statement.”

       But then so was the green button-down with the rolled-up sleeves with flat-fronted pants he wore on the cover of Milestones the previous year, an uncommonly confident and uncompromising pose -look at that stare – for a black jazz artist at the time. In fact, Miles was showing that he could carry off any number of shirt combos – collarless with a scarf or ascot, a scalloped collar under a seersucker jacket and checked, open-necked numbers, which were a particular favourite for a while.

       On stage, the Ivy League look of plaid jackets and trim trousers quickly gave way, especially after he had performed in Italy, to a clean, European style of slim-cut dark suit with unfussy white shirt and narrow tie. A pocket handkerchief was usually provided a flash of colour. This outfit, with subtle changes to jacket length and profile, would see him through the sixties and the years of his peerless Second Classic Quartet (Shorter, Hancock, Ron Carter, Tony Williams, Miles). Check out its ’64 concert in Milan on YouTube. It is the timeless Miles look almost all of us think of when his name is mentioned.

As the sixties ended, so his music started to change again, this time even more radically, and Miles would evolve his performance wardrobe with it. The exquisite ballads, the Harmon mute and the complex but satisfying Wayne Shorter tunes were phased out; processed trumpet and long jams came in. This gradual change to electric Miles (which began, tentatively, on 1968’s Miles in the Sky and reached its apotheosis on Bitches Brew in 1970) risked alienating older fans with a genuinely innovative, if often jarring, sound that was courting a new rock audience. So what?

          As the music became more groove-based and melody-free, Miles’ stage outfits morphed to reflect the dense patchwork that producer Teo Macero and Davis created from disparate tracks spliced together in the studio. By the time of the once much-derided but now feted funk-draped On the Corner in 1972, we had the furs, the cobra skin, the wrap-around sunglasses, suede trousers and the broad-shouldered, fringed leather jackets. Miles was still ahead, but few wanted to follow, unless they were self-assured enough to carry it off (as Lenny Kravitz and Prince eventually did).

       Interestingly, Miles might have invested in flamboyant outfits from the likes of Kohsin Satoh and Issey Miyake in later years, but he never fully abandoned the shirt. There is a famous photograph by Anthony Barboza of Miles in front of his wardrobe and a cascade of belts, scarves and shoes that almost looks as if someone has tossed a hand grenade into it. But, amid the African-inspired tops and leather trousers, in the top left-hand corner.. what’s that? A row of long-sleeved white shirts, of the sort he wore during the Kind of Blue sessions. In Michael Stradford’s book MilesStyle Barboza told the author that the trumpeter still liked expensive shirts but if he wore them in concert, they would get so sweaty “he’d throw them away. So, you never saw him in the same shirt twice. And he wasn’t spending $20 on them.” Maybe that’s why, eventually, they stayed in the wardrobe.

      Miles died in 1991, aged 65, by which time he had gone back to ballads (Human Nature, Time After Time) and had finally come to terms with his past, even exploring, thanks to Quincy Jones, some of his fabulous Gil Evans-arranged  recordings (from Miles Ahead, Sketches of Spain and Porgy & Bess) at a Montreux concert shortly before he died

        The mercurial, oft-troubled trumpeter was, as he admitted in his memoir, far from a perfect human being. Nevertheless, Miles changed the face of jazz across five decades as well as re-calibrating public opinion in the US about what a black musician could achieve – prestige, adulation, wealth – and how they could influence the wider public’s tastes. Most jazz people are remembered for a single thing, one great album or evergreen tune. Miles’ legacy is a dazzling kaleidoscope compared to others’ monochrome. Why the restlessness that dominated his life? “I have to change,’ he once said. “It’s like a curse.” And, in the end, our good fortune.

The Dartmouth Arms is on York Rise, NW5. The session is free. If you want to know more about Kind of Blue and its lasting influence I heartily recommend Richard Williams’ The Blue Moment.