From its Depression-era origins as a men's fashion magazine with high literary aspirations, through a brief period when it threatened to devolve into a semi-girlie pulp magazine, Esquire emerged by the 1960s as one of America's brashest and most sophisticated monthlies, with hard-hitting articles by the nation's leading writers and journalists on the hot-button cultural and political issues of the decade. At the same time, the periodical served as a Baedeker of sorts to a new generation of leisure-driven, style-conscious, sexually sophisticated men who were abandoning the austerity of the 1930s, the wartime privations of the 1940s, and the conformity of the 1950s for the more carefree, swinging lifestyle of the 1960s.

Esquire magazine was founded in 1933 by Arnold Gingrich and David Smart, who conceived of the publication as a magazine for the "new leisure," one that would be distributed largely through men's clothing stores, a plan that...