President John F. Kennedy and his family defined classic casual style, whether on the water at Hyannis Port, Massachusetts or in the rural Virginia countryside near Middleburg. The home movie footage below captures the Kennedy sense of ease and comfort while at play.
A few years ago on Ivy Style, Christian Chensvold published Jack and John: The Sartorial Dichotomy of JFK. This is an interesting essay on Kennedy’s use of clothing to build a public image that, in many respects, was a rejection of the conservatism of the Eisenhower era.
Kennedy was educated at several elite schools, Choate and Harvard (with a brief stint in an MBA program at Stanford), and his manner of dress was very Ivy League. As he entered public life and pursued politics, he became aware of the class associations of that style and, fearing that it might alienate certain voters, opted for a hybrid style that combined the apparel of preppy leisure with a more modern presentation in his role as Chief Executive, as Chensvold writes,
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 makes 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.
In 1956, while was serving his first term in the United States Senate, JFK made a bid for the Vice-Presidential nomination at the Democratic National Convention in Chicago. Although his bid fell short, losing to Sen. Estes Kefauver of Tennessee by just 38.5 votes, JFK became known as a rising star to millions of Americans. He spoke twice at the cenvention, placing Adlai Stevenson’s name in nomination for the Presidency and later giving a gracious concession speech (@ 23:41) after losing the Vice-Presidential nomination. Stevenson lost the general election that fall, as President Eisenhower was re-elected in a landslide.
As Chris Matthews of MSNBC’s Hardball commented, “In the 1950s, politics meant men in gray flannel suits – guys like Dwight Eisenhower, Robert Taft, Adlai Stevenson, and Richard Nixon. They were dull, stodgy…sexless.” All of that changed in November 1960 when JFK was elected President at 43 years old, the youngest man ever to occupy the White House. Aside from JFK’s political accomplishments during his tragically short term in office (1961-1963), he became one of the undisputed style icons of the 20th century.