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The Icon: JFK Jr.

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...

This one finds John at 15, with an unruly mop and a preppy V-neck—par for the course for a 10th-grader. For most of his life, he was known for well-groomed perfection—never a hair or a thread out of place—but it’s good to remember he could pull off unruly style just as well.

This is “prep” taken literally. Add a crested blazer, and this was the school uniform for Ivy feeders like Exeter, Choate and, in John’s case, Andover. Add in the New England ’fro and you’re pretty close to Take Ivy’s platonic ideal.

A cotton suit and a Manhattan summer circa 1989. And unless we’re mistaken, his tie matches his girlfriend’s dress.

The ’90s incarnate. This version of JFK Jr. could have stepped out of a J. Peterman catalog, complete with billowing shirt and mysterious bundles. But thanks to a good pair of shades and the literal kind of swagger, it all still works.

And most importantly of all, the man could wear a tux. His hair’s impenetrable without going full Gekko, the bow tie is elegant without being fussy, and everything fits perfectly. This is how it’s done.