John F. Kennedy Jr. may have been People's Sexiest Man Alive (1988), but when it came to his personal style, the political heir was less than award-winning.

Steven M. Gillon, friend of the late Kennedy and author of America's Reluctant Prince: The Life of John F. Kennedy Jr., told us, with a laugh, that he'd describe John's aesthetic as "sloppy."

"The thing about John is, when he needed to dress up and put on a tailor-made suit he looked like Superman, but just everyday … John's clothes, they didn't match, they didn't fit right, he always wore clothes that seemed to be about two sizes two big."

It's ironic, then, that Kennedy wed a woman so entrenched in the fashion world. Carolyn Bessette was a publicist for Calvin Klein.

"He was a slob who didn't care about the way he looked," Gillon continued, adding that this was an attitude that also existed at Kennedy's alma mater, Brown University. "The wealthiest kids at Brown, you could always tell because they're the ones who dressed like slobs. It was kind of a reversed elitism like those of us who are trying to be respectable, we always try to look nice, but John knew he didn't have to. When he wore clothes they would be mismatched and oversized."

If Gillon's description sounds familiar, it's because it's dangerously similarly to the definition of the scumbro trend: rich man wears whatever he wants; looks ridiculous (e.g. Pete Davidson, Justin Bieber).

Was JFK Jr. the original scumbro? You decide.