Here is F. Scott Fitzgerald, Author of “The Great Gatsby,” in Drag, ca. 1916

These photographs were taken in 1916 and depict F. Scott Fitzgerald dressed in drag to promote his college musical-comedy troupe’s performance of The Evil Eye at the Princeton Triangle Club. The young Great Gatsby author was in his third year at Princeton University and The New York Times on January 2, 1916 reviewed his performance positively— calling him “the most beautiful girl” in the production.

Fitzgerald posing for publicity photos for The Evil Eye, a musical he wrote in 1916 for the Princeton Triangle Club.

Fitzgerald had dropped out of Princeton to serve in the army—but he never actually saw combat. Soon after the U.S. entered the war in April 1917 he signed up for three weeks of military training and took the officer’s exam. He returned to school in September but soon received a commission as second lieutenant in the infantry and reported for training to Fort Leavenworth, Kansas, in November. (The captain in charge of his training platoon was Dwight D. Eisenhower.)

During 1918 he was stationed at Camp Zachary Taylor, near Louisville, transferred to Camp Gordon in Georgia, and then to Camp Sheridan in Alabama. When the war ended on November 11, Fitzgerald’s regiment was still waiting to embark for France. He was discharged from the army in February 1919.