Miles Ahead

Timeless Style by the Warlord of the Weejun

Whether jazz is your thing or not doesn’t matter; the fact is, Miles Davis in the late 50s and 60s was one of, if not the best-dressed pop cultural icons for the sartorially inclined.

His influence remains strong in 2024 and will continue for decades to come.

I’m obsessed with his style and his music. To be honest, it doesn’t feel right that I haven’t dedicated an article to him yet, so let’s change that.

Miles was a forward thinker in every sense—his music, his outlook, and of course, his clothes. “Ivy style” was the vogue of the early 60s. Musicians all wanted that look. They saw the upper-middle-class white Americans wearing it, with its aura of success, and they desired it too. Miles Davis flew the flag and paved the way for a whole movement that followed.

See-ya suckers!

The Newport Jazz Festival in 1958 is often regarded as a pivotal moment in jazz history, particularly due to Miles Davis's electrifying performance.

What also made Davis stand out above the rest was what he was wearing. Seersucker and sunglasses waved goodbye to the stuffy neutral tones of the past. Jazz had entered a new age.

As Miles wandered the festival, no tie was worn around his neck, but a camera. He exuded the look of someone who wasn’t there merely as a performer but as a disciple of music. He was there to live and breathe it, to capture it and learn.

"I’m always thinking about creating. My future starts when I wake up every morning."

It’s no surprise that photographer William Claxton would use Miles Davis as his subject for a series of photographs.

Claxton was known for shooting the likes of Chet Baker and Steve McQueen, forging friendships with these stars along the way.

There’s a line that runs parallel between McQueen and Davis; they were both cut from the same cloth.

Miles Davis often defied musical conventions, pushing boundaries and exploring new styles throughout his career, from bebop to jazz fusion. Steve McQueen was known for his unconventional roles and rugged persona, often challenging Hollywood norms. His nonconformist attitude made him a symbol of the "cool" anti-hero.

The Warlord of the Weejuns

His obvious devotion to Ivy style, adopting pieces such as Bass Weejun loafers, earned him the title “Warlord of the Weejuns” in Esquire writer George Frazier’s liner notes for the Miles Davis’ Greatest Hits album.

In those notes, Frazier recounts a conversation with Miles after he came off stage in French Lick, Indiana.

“He asked me how I thought he’d done. “You sounded superb. You—” But he stopped me. “No, not that,” he said. “I mean how did my suit look?”

In comparison to many musicians today, Miles always looked ready to perform without appearing to be trying too hard. There are numerous shots of him either rehearsing or minding his own business, seemingly unaware he’s having his picture taken, and they continue to serve as inspiration.

One standout image for me is the photograph below, where Miles is captured by Michael Ochs recording the album Quiet Nights with producer Gil Evans in New York, August 1962.

Miles takes a moment to light a cigarette while Gil either conducts the band or waves his hands in frustration. We’ll presume he was conducting.

Miles appears to be wearing a popover shirt with a generous collar roll underneath a jacket with a mandarin collar, perhaps made of suede—very much a fashionable piece of menswear in the early 60s.

Miles Davis taught rockstars how to be rockstars. He embodied the archetype of the "cool" musician. His confident, sometimes rebellious demeanor set a precedent for the rockstars who followed. He demonstrated that being an artist was not just about the music but also about cultivating an image and persona.

One lesson Miles Davis teaches us well is not to emulate. You could look at all these pictures and think, “I’m going to recreate that look.” But that’s not how he would have done it. He may have been influenced by Ivy style, but he certainly made it his own. Whatever he wore, it was Ivy style worn by Miles Davis—not Ivy style worn by anyone else.

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Thanks for reading,

Tom