Miles Davis’s free flowing, highly evolved trumpet playing laid the groundwork for the evolution of jazz, pushing it into experimental territories. In the process he made himself into one of the most recognized and important musicians of the 20th century. But it’s not just with his instrument that Davis cut a stylish path. Well aware not only of being constantly in the public eye but also of the disadvantages he faced due to the inherent racism that flowed through the culture, Davis was equally smooth with his appearance as he was his music.
While not afraid to keep up with the fashion of the times—or lead its charge by dressing in high fashion designers’ experimental visions, as he did in the late ’60s and ’70s—he still managed to make every look his own with an impeccable sense of self. As a man, Davis was so comfortable with himself and oozed style so completely that he managed to transform any clothing he wore into a second skin, assimilating it into his own sense of style rather than allowing the clothes to make the man. He also knew that, with the public’s eyes always upon him, their perception of his musical acumen would in some way be shaped by his appearance.
Davis is best remembered for his role in the formation and evolution of cool and experimental jazz in the ’50s and ’60s, and we’re still feeling the fallout, both culturally and artistically. Here’s how to dress like a jazz impresario from one of New York’s hippest periods.
Up through the ’60s, musicians primarily wore suits on stage, just as in the broader culture most men wore them every day. While he famously started out rocking second-hand Brooks Brothers suits, Davis ultimately favored a slimmer, European, tailored cut. As he ventured into more expansive and experimental musical realms, his suits also transformed. When he adopted a lean silhouette that could be described as preppie or Ivy League, Davis was at the forefront of both music and fashion. Dapper, clean lines, never boxy like the ’20s era suits many swing and big band musicians wore. It’s still a valid look—a good fit is timeless. Zara makes a great ensemble for men on a budget, but if you want to treat yourself, Dolce & Gabbana’s slim stretch wool suit will have you looking like the coolest cat on the block.
One of the ways Miles and his crew set themselves apart from the previous generation was by ditching the staid lace up dress shoes and opting instead for loafers or boat shoes. Davis’s favorite? The Bass Weejun, which you can get hold of for relatively cheap. Want to spend like a jazz icon? Try Ermenegildo Zegna’s deerskin Avenue loafers, and you’ll be as smooth as they come.
As immortalized by the cover of his classic 1958 album, Milestones, the green Oxford shirt is a perfect ode to the jazz legend. Try Harry Stedman’s Reed Green Oxford, admittedly inspired by Davis, for a good fit. Just don’t expect to exude anywhere near the same amount of cool.
Gotta be knit, textured like the music. Davis himself wore the Brooks Brothers woven ties, or, in an even more revolutionary (for the time) move, no tie at all. Which brings us to…
Okay, so the turtleneck is a piece that has to be done right. Don’t be crazy and wear a necklace or something with it, and stick to casual, but not baggy fitting, unless it’s a heavy knit, like Orvis’ wool and cashmere blend Donegal. Helmut Lang’s Core Cashmere turtleneck is an easy “yes,” as is Belstaff’s impeccable Littlehurst.