Bobby soxers were a subculture of young women in the mid-to-late 1940s. Their interests included popular music, in particular that of singer Frank Sinatra, and wearing loose-fitting clothing, notably bobby socks. Their manner of dress, which diverged sharply from earlier ideals of feminine beauty, were controversial. As a teenager, actress Shirley Temple played a stereotypical bobby soxer in the film The Bachelor and the Bobby-Soxer (1947).

Francis Albert Sinatra was an American singer and actor. Nicknamed the "Chairman of the Board" and later called "Ol' Blue Eyes", he is regarded as one of the most popular entertainers of the mid-20th century. Sinatra is among the world's best-selling music artists, with an estimated 150 million record sales globally.