Dressed for the day
I keep thinking that maybe part of the appeal was exactly that he did not seem too concerned with building an image. Or at least he did not seem interested in looking like someone who was building one.
There is something very specific in the way he looked dressed. Not sloppy, not formal, not casual either. More like someone mixing the day he had with the rest of his life. A work shirt with something more ordinary. A blazer with a cap. Good trousers with shoes that did not feel precious.
He looked like he had other things on his mind.
It gave the impression that he got dressed to move through the city, not to be looked at in it.
When ease becomes a uniform
Maybe that is why it still feels attractive now. Not because the clothes were revolutionary, but because the whole thing seemed unforced. Like he was trying to pass through the day without making too much of a point, even if the result ended up becoming a point anyway.
The problem is that a lot of people are now thinking too much about the JFK Jr. aesthetic as a finished Pinterest idea, and not enough about what made it convincing in the first place. The charm was never just the shirt, the blazer or the haircut. It was the impression of a man who looked like he had other things on his mind.
When too many people try to copy it exactly, what is left is only the uniform. Maybe the most interesting thing about him was that he never seemed to dress like one.