Five style lessons to learn from the late JFK (2024)

The late John Fitzgerald Kennedy is arguably best remembered for his untimely death by assassination in 1963, for his alleged affair with Marilyn Monroe and for being one of the most handsome American presidents to date. But his memory also perseveres because his personal style was just so spot on.

Unlike the current Potus, who has a penchant for ill-fitting slacks, too-long ties and caps that even Kanye West can’t get away with wearing, JFK served consistent, 1950s prepster goodness.

Having enrolled at both Princeton and Harvard universities, JFK’s wardrobe was tinged with an Ivy League sensibility that was prevalent within upper-middle-class families at the time. Long before Tyler, The Creator, JFK was the nation’s leading advocate for chinos, army surplus khakis, grey marl sweatshirts, penny loafers and Oxford shirts.

Below are the style lessons you can learn from arguably America's best-dressed president.

1. The shorter the shorts the better

Hy Peskin Archive

JFK was known for jet-setting in his personal time, frequenting far-flung places such as Acapulco, (he and Jackie Kennedy honeymooned here), the Kennedy Compound in Hyannis Port, Massachusetts, Johns Island, Maine and Marrakesh.

And, in turn, he perfected his summer-vacay wardrobe. Long before Harry Styles and Paul Mescal were schooling men on how to go about wearing shorts, JFK was the man to look to for cut-off inspiration. The main attraction in JFK’s vacation wardrobe being, of course, a pair of thigh-high shorts, he was nailing trends before the big catwalk brands even knew they were trends.

The trick to steal here? Go short (about 2cm above your knee) and wear with ribbed socks and a pair of GH Bass & Co Weejun loafers.

2. A skinny tie isn’t all bad

Alfred Eisenstaedt

Five style lessons to learn from the late JFK (2024)
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