Cluett, Peabody and Company, And Now the Shorts with the Seamless Crotch Go Gay!
This underwear ad appeared in the Spring 1933 Apparel Arts: Fabric & Fashions (Vol. II, No. 3, p. 11).
While the use of the word gay to mean "homosexual" instead of "happy" or "colorful" came into usage in the late 1960s around the time of the Stonewall riots in New York City, its origins do go much further back. A 1933 slang dictionary defined a "gaycat" to mean a homosexual boy (Ersine 1935; date confirmed by New York Times Magazine "On Language" columnist William Safire Nov. 6, 2005), though its non-documented usage would predate publication. According to etymology web site wordorigins.org, the term was "being used by homosexuals to refer to themselves with certainty as early as the 1920s, and possibly as early as the 1860s."
It continues, "The first unequivocal written use of gay to mean homosexual is in 1929, in Noel Coward's musical 'Bittersweet' -- four overdressed, 1890s dandies sing the song 'Green Carnation.' 'Gay' appears again in 1933 in Ford and Tyler's 'Young & Evil.' In 1938 in the movie 'Bringing Up Baby,' the character played by Cary Grant, when asked why he is wearing women's clothing replies, 'Because I just went gay all of a sudden.' In retrospect, this is obviously a joke intended to slip past the censors. In their 1941 book 'Sexual Variations,' Gershon Legman and G.V. Henry cite 'gay' as a slang term for homosexual, which indicates that it was in use for some time prior."
Thus, this ad appears to be an amusing look backward at the word's intriguing usage in a locker room setting about underwear and crotches, in a message to fashion-conscious men -- often thought of as gay.