Trippe attended the Bovea School and graduated from the Hill School in 1917. He enrolled at Yale University but left when the United States entered World War I to apply for flight training with the U.S. Navy. After completing training in June 1918, he was designated as a Naval Aviator and was commissioned as an Ensign in the U.S. Naval Reserve. However, the end of World War I precluded him from flying in combat. Demobilized from active duty, he returned to Yale, graduating in 1921. While there, he was a member of St. Anthony Hall and of the Skull and Bones society. Trippe was treasurer at the first-ever meet of the National Intercollegiate Flying Association in 1920.