Miles Davis was the best-dressed man of the 20th century. Starting out, he’d customise his pawnshop Brooks Brothers suits, cutting notches in the lapels in imitation of the Duke of Windsor. After 1949’s Birth of the Cool, he favoured the Ivy League look of European tailoring. In the 60s he went for slim-cut Italian suits and handmade doeskin loafers. He was always the coolest-looking man in the room. Hell, he even managed to look cool sporting a blood-splattered white khaki jacket following a scuffle with police outside Birdland. In the 70s his wardrobe went as far-gone funky as his music and he was the only man who could get away with wearing purple bell bottoms, kipper ties and hexagonal glasses.
The Cool World by Shirley Clarke featuring The Dizzy Gillespie Quintet, 1963