The ’90s were a different time. Simpler, even.

It’s still a bit of a style taboo, but at its best, ’90s style was a retake of the same optimistic ennui that drove the early ’60s—so it’s only right that its greatest icon would be a latter-day Kennedy, a man of leisure in an increasingly uncertain time.

Ladies and gentlemen, JFK Jr.

If you look through these pictures closely enough, you’ll see most of the decade represented, from RL prep to Wall Street insouciance. Of course, he bowed out too soon (just as the decade ended, in fact), but what’s left is a remarkable record of a man in his prime. Here are a few of our favorites…

Our five favorite pics of JFK Jr.»
 

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