One of the leading candidates for “Nattiest Dresser of the 20th Century” might well be Arthur Schlesinger, Jr. He graduated from Phillips Exeter, perhaps the most elite prep school in America. He was also an alumnus of Harvard, serving on the faculty there before going to work for the Kennedy administration in 1961. Designated as Special Assistant to the President, he functioned as a roving intellectual in the White House, advising Kennedy on a number of matters, particularly Latin American affairs. Schlesinger was rarely seen without his trademark bow tie and P3 tortoiseshell glasses.
John Fitzgerald Kennedy’s first political campaign came in 1946 when he ran for Congress in the 11th District of Massachusetts. He was 28 years old, a graduate of Harvard University and a veteran of WWII, having served as a PT Boat commander in the Pacific Theatre. He was recognized for heroism, helping to save his crew members after being rammed by a Japanese destroyer.
Kennedy is shown here relaxing in a chair below one of his campaign posters. Photographs of his mom, Rose, and his father, Joseph, are on the mantle. He is wearing a white shirt with a rep tie and gray flannel pants. When inaugurated as President of the United States in 1961, Kennedy brought a dramatic improvement in style to the White House.