On assignment for the online magazine at RalphLauren.com, Ivy Style founder Christian Chensvold muses on that brief point in time when jazz musicians went for the clean-cut look, which, considering many of them were junkies, was the only clean thing about them.

Sometime around 1954, jazz great Miles Davis walked into the Andover Shop, a small haberdashery in Cambridge, Massachusetts, and single-handedly turned the world of style upside down. Just as his groundbreaking album Milestones (celebrating it’s 50th anniversary next year) changed music, that afternoon in Cambridge shifted men’s fashion.

Miles emerged from the store clad head to toe in traditional “Ivy League”–style clothing, and in so doing merged two separate worlds—those of the establishment and the black jazz artist—as if fusing two dissonant notes to create a bold new harmony. The result was a crashing chord of cool that obliterated the line between square and hip, sounding a fashion fortissimo that lasted several years before fading into the silence of pop-culture obscurity.

Miles stocked up on tweed and madras jackets with a natural shoulder and narrow lapel; chino and flannel trousers; button-down shirts; knit and regimental striped ties; and Bass Weejun penny loafers. “It was a look that redefined cool,” writes Miles biographer John Szwed, “and shook those who thought they were in the know.”

“It sounds corny now,” recalls 82-year-old Charlie Davidson, who still runs the Andover Shop, “but Miles liked the real Ivy League look, and it became the hip way of dressing.”

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