Photographs of John F. Kennedy generally fall into two categories. In the first, we see him at his family’s Cape Cod retreat, sleeves rolled up, wearing khakis grass-stained from touch football, or clad in Nantucket Reds and sunglasses sailing the sea. In the second, his presidential kit, we see another man altogether. Kennedy’s dark suits hang with a certain awkwardness, the shoulders large and high, his two chest buttons both fastened.
Though both are equally iconic, these two images of JFK reveal the sartorial differences between the man’s public and private lives. Privately, he was the Choate- and Harvard- educated scion of a patrician American dynasty, while publicly, he was a progressive young Democrat, commander on the frontlines of the Cold War, and careful crafter of a public image in the new age of television.
This schism made JFK both the ultimate preppy President — his administration reigned at the height of the Ivy League Look — and an ironic hastener of the look’s decline, undermining the very style he so perfectly embodied. Though Kennedy could hide neither his Catholic faith nor his Brahmin accent, this first great image crafter of the TV age strengthened his broad appeal with two sartorial gestures: He would wear two-button suits instead of three-button sack models, and he would eschew buttondown collars. The result, noted LIFE magazine in 1961, was that the President’s clothes “fail to conform to current Ivy League fashion”.
Before becoming a style setter, Kennedy started out as a ragamuffin. “As a young man he was notorious for his personal disorder,” writes Neil Steinberg in his book Hatless Jack: The President, the Fedora, and the History of American Style. “His boarding-school roommates complained of his messiness, particularly with clothes. He would show up with his shirt untucked, or without socks, or wearing a rag of a necktie.”
Prior to his marriage to Jacqueline Bouvier in 1953, “Kennedy had been a sloppy dresser who favoured baggy suits clashing shirts and ties, and ratty tennis shoes,” according to historian Thurston Clarke.