Additionally, Jackson's Republican political viewpoints contrasted with the liberal Democratic views of Smart, which allowed for the magazine to publish debates between the two.

[6] However, demand was so high that by its second issue (January 1934), it transformed itself into a more refined periodical with an emphasis on men's fashion and contributions by Ernest Hemingway, F. Scott Fitzgerald,[7] Alberto Moravia, André Gide, and Julian Huxley.

In the 1940s, the popularity of the Petty Girls and Vargas Girls,[8] particularly among the Armed Forces provided a circulation boost, but also proved controversial: in 1943, the Democratic United States Postmaster General Frank Comerford Walker brought charges against the magazine on behalf of the administration of Franklin Delano Roosevelt,[9] which alleged that Esquire had used the US Postal Service to promote "lewd images".

[8] Beginning with its second number, a blond, pop-eyed, mustachioed character named "Esky" (created by cartoonists E. Simms Campbell and Sam Berman), graced almost every Esquire front page for over a quarter of a century, depicting the refined character of the magazine and its readership, mostly in the form of figurines, although a stylized design of his face would often appear as well (replacing the figurines in the 1950s), and beginning in 1962, this graphic would be featured as the dot on the "I" of the logo until this was changed in 1978.

Under Harold Hayes, who ran it from 1961 to 1973, Esquire became as distinctive as its oversized pages,[13] helping pioneer the trend of New Journalism by publishing such writers as Norman Mailer, Tim O'Brien, John Sack, Gay Talese, Tom Wolfe, and Terry Southern.

In the mid-1960s, Esquire partnered with Verve Records to release a series of "Sound Tour" vinyl LPs that provided advice and music for traveling abroad.

The arrival of male-oriented lifestyle publications during the early 1990s and the problems of the magazine industry during the middle of the decade led to a sustained decline in circulation that threatened the future of Esquire, which had relied upon an elegant, highly-literate audience (until the late 1970s, it published a "back-to-college" issue each September, and during the second half of the 1980s it published a year-end register featuring leading cultural figures under 40 years of age) but did not appeal to younger men.

David M. Granger was named editor-in-chief of the magazine in June 1997, fresh from a six-year stint at GQ, which he turned around from its fashion-heavy tradition.

Each morning the editors of the magazine recommend one thing for readers' immediate enjoyment: "not a political candidate or position or party, but a breakthrough idea or product or Web site.

Lish helped establish the career of writer Raymond Carver by publishing his short stories in Esquire, often over the objections of Hayes.

Using the influential publication as a vehicle to introduce new fiction by emerging authors, he promoted the work of such writers as T. Coraghessan Boyle, Barry Hannah, Cynthia Ozick, Reynolds Price and William Harrison.

"[21] Other authors appearing in Esquire at that time included William F. Buckley, Truman Capote, Murray Kempton, Malcolm Muggeridge, Ron Rosenbaum, Andrew Vachss and Garry Wills.

Writer Elizabeth Gilbert debuted in Esquire in 1993, while Chris Adrian, Nathan Englander, Benjamin Percy, and Patrick Somerville among others have also contributed to the magazine.

Rick Moody, Jonathan Ames, Bret Anthony Johnston, Joshua Ferris, Yiyun Li, Aimee Bender, and ZZ Packer are among the notable writers included.

However, the February 2006 "Dubious Achievement Awards" used the caption under a photo of W. Mark Felt, the former FBI official revealed in 2005 to be "Deep Throat", the source for Bob Woodward and Carl Bernstein to uncover the Watergate scandal.

[25] Waldman said the profiles "traffic in weirdo pious metaphors and exaggerations that aim to winkingly indicate how overcome a guy gets in the face of a gorgeous lady.