According to Wikipedia, this is a yearbook photo from Kennedy’s time at Boston Latin School. but other sources give a date of around 1913, which was the year before his marriage to Rose Elizabeth Fitzgerald.
John F. Kennedy (left) and his elder brother Joseph Patrick, in May 1942. In this picture, it was Joe who was the “President in Waiting”. Their father, Joseph P. Kennedy, Sr, was in the political wilderness because he had supported Neville Chamberlain’s appeasement of Hitler and the Nazis, and he placed all his political ambition on the shoulders of Joe. When Joe was killed in 1944, that ambition was transferred to the next son, JFK.