Never Knowingly Underdressed.
When Miles adopted the clothes considered the reserve of the Ivy League elite, he wasn’t just embracing a compelling style, he was challenging the status-quo – one which that particular mode of dress seemed to represent.

It was an act of stylistic subversion, a contrafact, a sophisticated cultural hi-jack.
He was also returning to many of the stylistc references he'd grown up wearing as a young man, prior to his move to New York in his late teens.

By contrast to what he'd witnessed in Europe, in some parts of America this was still the era of Jim Crow...

...Segregation and the Klu Klux Klan....

By putting on those weejuns, that button-down, that seersucker jacket, that blazer and those khakis, he was elegantly undermining the establishments illusion of superiority.

He'd walked into an exclusive club uninvited and used those clothes to send out a message while laughing in the face the endemic prejudice of the time. Many other jazz musicians were to follow him.

I never have forgotten one time in Europe this nice old man told me how in World War II, the Europeans didn't know what to make of Negro troops. They had their picture of this country from our magazines and movies, and with a very few exceptions like Pops Armstrong and Joe Louis and Jesse Owens, they didn't know about any Negroes except servants and laborers.

Born on May 26, 1926, had he lived Miles Davis (pictured far left) would have been 85 years old today.
So What.