Miles Davis was a vital force in the evolution of jazz, amassing critical praise, pioneering movements like bebop and jazz fusion, and ultimately changing the game for his peers. But while his career was rooted in a complex world of rhythm and melody (he produced the best-selling jazz album in history, 1959's Kind of Blue,), his dress reflected a simpler notion of cool. In the same way he managed to reinterpret old standards so that they suddenly sounded fresh, Davis made the sedate uniform of the '40s -- pressed khakis, knit top, dress shoes -- pop with effortless flair (take that scarf, for example). Davis knew it wasn't what you do, but how you do it, that mattered. "For me," he said in 1989's Miles: The Autobiography, "music and life are all about style."
Photography by Jonathon Kambouris
2. Navy cool wool polo sweater by Brioni, $795
3. Oval shank ring in sterling silver by David Yurman, $350
4. Khaki Wader by Dockers, $52
5. Suede ankle boots by Louis Vuitton, $995