Swing Like Miles

On West 77th Street, half a block from the Hudson River, lies a nondescript townhouse, five floors counting the garden level and no bay window denoting the parlour floor, though one on the third floor. A pleasing yet plain brick and stone facade hides the house’s history. It once belonged to Miles Davis.

Davis’ West 77th Street townhouse lies six blocks from my Upper West Side apartment. The beautiful neighborhood isn’t hip. Yet it possesses an old New York sangfroid that lies in its preservation and anonymity. Waves of teardowns haven’t crashed upon the Upper West Side, unlike many neighborhoods downtown and in Brooklyn. Relatively untouched by time, preserving the past while looking toward the future like many places in New York do. It’s no surprise Miles lived here in his creative heyday, from around 1960 through the early 1980s, in the middle of the scene yet away from it all.

The Upper West Side exemplifies nonchalance. It’s not as stuffy as the proper, opulent avenues of the Upper East Side, yet just as grand. An air of assuredness exists here that only longtime New Yorkers possess. I look on in awe as a newcomer. The neighborhood is clothed in rumpled intellectualism, not ill-fitting but lackadaisical and elegant. Book editors and businesspeople wear their Ralph Lauren jackets and trousers they’ve owned since the ‘80s or ‘90s, with a Brooks Brothers shirt that has withstood decades of incremental weight gains and losses, never getting too loose or too tight. The more audacious wear bespoke guayaberas with off-white chinos on their daily shopping trips to Zabar’s.

Miles’ style exemplified the buttoned-up, sometimes untucked cool that is the Upper West Side. No one confuses it for of-the-moment. Rather it’s timeless, a look that resonated yesterday, that resonates today and tomorrow. Somehow it’s ahead of the curve despite its roots in tradition. There are garments that defined Miles’ cool yet there is no blueprint for achieving it. Miles wasn’t a type. You can’t be Miles. You can’t dress like Miles because you don’t have his attitude.

Yet finding inspiration in Miles’ style is worthwhile. He looked the part of the cultured New Yorker ready to make the scene, wearing conservative clothes in a liberal manner. The shirt Miles wore didn’t matter as much as the way he wore it. On the cover of 1958’s Milestones, you see Miles’ tones on full display, front and center in a seafoam green oxford shirt and dark gray trousers. Every male Ivy League student of the era wore a similar look, but without the ease and subversiveness that Davis did. Where did his jacket go? The trousers look like part of a suit, yet bringing in the jacket would disturb the look. The shirt’s details are immaculate, from the beefy collar roll to the durable stitching, the crisp sleeve roll to the unconstricted yet flattering fit.

Speaking of Davis’ suits and jackets, they were single-buttoned, designed to his specification. One photo of Davis from 1966’s Newport Jazz Festival shows the trumpeter in motion, looking, in his words, “Cleaner than a broke dick dog” in a notch-lapel, single-buttoned double-breasted ensemble. Derived from Ivy simplicity, the cut was more urbane and fitted than its sack-suited siblings. Miles’ spread-collar shirt, trim tie, and crisp pocket square are melody notes anchoring an improvisation on a familiar theme. An ample amount of cuff is visible, but not to the extreme of Sammy Davis, Jr. Beneath the cuff, Miles’ watch sits subtly. Before switching to a large Breitling Navitimer in the late 1960s, Miles sported a rectangular watch, either a Cartier Tank or a Jaeger-LeCoultre Reverso, both paragons of simplicity that make the case for discretion.

Less discrete was Miles’ style during his electric period. Miles became flashier while building on his natty roots, amplifying the pieces he had wore in a silent way for years. A devotee of ascots and scarves, these neck coverings rooted his wardrobe as he morphed with the times. He had sported them since the 1950s, and an iconic photo of Miles from the era shows him wearing a trim gray long-sleeve polo sweater, off-white trousers, black leather chukka boots, and an elegant scarf framing his face. As the ‘50s turned to the ‘60s turned to the ‘70s, Miles wore ascots and scarves over and underneath untucked shirts, sometimes adorning his bare chest. When Miles wore clothes, everything became looser, flowing in a bohemian manner. The trousers were still there, the shirts and jackets, whenever they were, were breezy and free.

Each turn in Miles’ style, musical and sartorial, had its foundation in his past. A photograph taken by Tom Palumbo shows a young Davis wearing a beefy oxford shirt with a formidable collar and slouchy sleeves rolled to imperfection. The shirt was paired with double-pleated, beltless trousers secured by a taut waistband. Though different garments than those that Miles wore in the 1970s, the nonchalant manner and basic styles remained the same, as did the idea of subverting heritage to his needs and specifications. While clear in Palumbo’s early photograph, Miles’ later looks have only achieved timelessness now. Though many of Miles’ ‘70s garments seemed futuristic, they became prescient, classic pieces that resonate with a new generation mining their parents’ icons for inspiration. They then become our icons, and old is cool again, a cool that can be reimagined but not rebirthed.

Don’t copy Miles’ look. Riff off it. Stepping into Brooks Brothers isn’t the same as it once was. The shirts are no longer made in America, the collars aren’t as glorious. Gems still exist in the store, mostly in the shoe department where you can find the sort of exquisite leather footwear Miles favored, like leather desert boots and penny loafers, sometimes unstructured, sometimes in cordovan leather. If you’re hell-bent on learning Miles’ moves and want to replicate him note for note, go vintage. Though Miles would hate you copying him. He’d want you to improvise.

There’s no Rebirth of the Cool, but Drake’s and Sid Mashburn carry on the spirit. Were Miles alive today, these are the places he’d shop. They’re the sort of traditional haberdashery that isn’t too buttoned up. They attract a formal crowd as well as daring, singular reprobates who want to make suiting and sportswear their own. They carry on the tradition of trim, but not slim, beefy-collared shirts with fine fabrics, trousers made for cuffing, shetland and cable-knit sweaters that add a dash of intellectual insouciance to fall outfits, silk knit and repp ties in all colors and stripes, and jackets and suits that stand the test of time. Wear them any way you like, so long as you’re not stiff as a mannequin and can swing in them.

“For to swing is to communicate, is to convey the rhythms of one’s own being,” said Norman Mailer in his essay The White Negro. That’s why the Upper West Side, where Miles once lived, is still swinging in a weird way, despite that hipness has bypassed it. The Old New Yorkers know how to communicate their being through style, and so did Miles. His style was singular and inimitable because his cool, his individuality, couldn’t be faked. Imitation isn’t flattery but tribute is. We learn from our heroes and icons but cannot copy them, for style is innate. Ask Miles, and he’d tell you not to copy his riffs, but improvise off them. And swing to your own rhythm.