Founded in 1933, it flourished during the Great Depression and World War II under the guidance of founders Arnold Gingrich, David A. Smart and Henry L. Jackson while during the 1960s it pioneered the "new journalism" movement. After a period of quick and drastic decline during the 1990s, the magazine revamped itself as a lifestyle-heavy publication under the direction of David Granger.
Esquire was first issued in October 1933 as an offshoot of trade magazine Apparel Arts (which later became Gentleman's Quarterly; both Esquire and GQ would share common ownership for almost 45 years). The magazine was first headquartered in Chicago and then, in New York City. It was founded and edited by David A. Smart, Henry L. Jackson and Arnold Gingrich. Jackson died in the crash of United Airlines Flight 624 in 1948, while Gingrich led the magazine until his own death in 1976. Smart died in 1952, although he left Esquire in 1936 to found a different magazine for the company, Coronet. The founders all had different focuses; Gingrich specialized in publishing, Smart led the business side of the magazine while Jackson led and edited the fashion section, which made up most of the magazine in its first fifteen years of publishing. 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. This grew particularly heated in 1943 when the Democratic United States Postmaster General Frank Comerford Walker brought charges against the magazine on behalf of the administration of Franklin Delano Roosevelt. The administration alleged that Esquire had used the US Postal Service to promote "lewd images". Republicans opposed the lawsuit and in 1946 the United States Supreme Court found in Hannegan v. Esquire, Inc., 327 U.S. 146 (1946), that Esquire's right to use the Postal Service was protected by the First Amendment of the United States Constitution.
Esquire initially was supposed to have a quarterly press run of a hundred thousand copies. It cost fifty cents per copy (equivalent to $9.88 today). 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, Alberto Moravia, André Gide, and Julian Huxley. In the 1940s, the popularity of the Petty Girls and Vargas Girls provided a circulation boost.
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 during the 1950s, an stylized design of his face would often appear. Beginning in 1962, Esky would be featured as the dot on the "I" of the logo until it was changed in 1978. After then, the character was relegated to the back pages of each edition, featuring witty phrases. During the 2000s, the magazine briefly held an annual "Esky" award focused on rock bands (with the character now having black hair, a leather jacket, a white T-shirt, jeans and a guitar). Following Esquire's 2016 revamp, the stylized Esky became featured more prominently, occasionally returning to his old spot in the logo.
Under Harold Hayes, who ran it from 1961 to 1973, Esquire became as distinctive as its oversized pages, 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. In August 1969, Esquire published Normand Poirier's piece, "An American Atrocity", one of the first reports of American atrocities committed against Vietnamese civilians. Like many other magazines of the era, Esquire shrank from the traditional large-magazine format (about 10-1/4"x13-3/8") to the smaller standard 8½×11 inches in 1971.
The magazine was sold by the original owners to Clay Felker in 1977 (although Esquire Inc. kept its name until its acquisition by Gulf + Western in 1983). Felker reinvented the magazine as a fortnightly in 1978, under the title of Esquire Fortnightly. However, the fortnightly experiment proved to be a failure, and by the end of that year, the magazine lost US$5 million. Felker sold Esquire in 1979 to the 13-30 Corporation, a Tennessee-based publisher, whose owners refocused the magazine into a monthly, beginning with the July issue (dated both as July 3 and 19). During this time, New York Woman magazine was launched as something of a spin-off version of Esquire aimed at a female audience. The 13-30 Corporation split up in 1986, and Esquire was sold to Hearst at the end of the year, with New York Woman going its separate way to American Express Publishing.
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. David M. Granger was named editor-in-chief of the magazine in June 1997. Since his arrival, the magazine received numerous awards, including multiple National Magazine Awards. Prior to becoming editor-in-chief at Esquire, Granger was the executive editor at GQ for nearly six years. Its award-winning staff writers include Tom Chiarella, Scott Raab, Mike Sager, Chris Jones, John H. Richardson, Cal Fussman, Lisa Taddeo, and Tom Junod. Famous photographers have also worked for the magazine, among which fashion photographer Gleb Derujinsky, and Richard Avedon. In spite of its success, the magazine under Granger became increasingly criticized for its focus on the so-called metrosexual culture (a criticism he previously had late in his GQ tenure). David Granger stepped down in 2016, being replaced by Jay Fielden, who revamped the magazine into its more classical up-market style. At the same time, its political coverage became more comprehensive, following a trend among American magazine publications in general.
In September 2006, the magazine launched a special style-focused issue entitled The Big Black Book, which beginning in 2009 was published twice a year. It stopped publishing after the Spring/Summer 2018 issue, continuing as a feature on the Esquire website.
In 2010, the June and July issues were merged as were the December and January issues in 2015, and in 2018 the magazine moved to eight issues per year. 
In January 2009 Esquire launched a new blog—the Daily Endorsement Blog. 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." The concept of the "Daily Endorsement Blog" was said to have emerged from Esquire's November 2008 issue called the "Endorsement Issue", in which, after 75 years, Esquire publicly endorsed a presidential candidate for the first time. The Daily Endorsement Blog was officially discontinued on April 2011.
From 1969 to 1976, Gordon Lish served as fiction editor for Esquire and became known as "Captain Fiction" because of the authors whose careers he assisted. Lish helped establish the career of writer Raymond Carver by publishing his short stories in Esquire, often over the objections of Hayes. Lish is noted for encouraging Carver's minimalism and publishing the short stories of Richard Ford. 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 and Reynolds Price.
In February 1977, Esquire published "For Rupert – with no promises" as an unsigned work of fiction: this was the first time it had published a work without identifying the author. Readers speculated that it was the work of J. D. Salinger, the reclusive author best known for The Catcher in the Rye. Told in first-person, the story features events and Glass family names from the story "For Esmé – with Love and Squalor". Gordon Lish is quoted as saying, "I tried to borrow Salinger's voice and the psychological circumstances of his life, as I imagine them to be now. And I tried to use those things to elaborate on certain circumstances and events in his fiction to deepen them and add complexity."
The magazine's policy of nurturing young writing talent has continued with Elizabeth Gilbert, who debuted in Esquire in 1993, and more recently, with the work of such writers as Chris Adrian, Nathan Englander, Benjamin Percy, and Patrick Somerville. Other writers who have recently appeared in the magazine and on Esquire.com include Ralph Lombreglia, James Lee Burke, and Stephen King.
The Napkin Fiction Project
In 2007 Esquire launched the Napkin Fiction Project, in which 250 cocktail napkins were mailed to writers all over the country by the incoming fiction editor, in a playful attempt to revive short fiction—"some with a half dozen books to their name, others just finishing their first." In return, the magazine received nearly a hundred stories. Rick Moody, Jonathan Ames, Bret Anthony Johnston, Joshua Ferris, Yiyun Li, Aimee Bender, and ZZ Packer are among the notable writers included.
Dubious Achievement Awards
For many years, Esquire has published its annual Dubious Achievement Awards, lampooning events of the preceding year. As a running gag, the annual article almost always displayed an old photo of Richard Nixon laughing, with the caption, "Why is this man laughing?" 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 the "Deep Throat" Watergate source for Bob Woodward and Carl Bernstein. The magazine did continue the Nixon photo in February 2007, referring to a poll stating that George W. Bush had surpassed Nixon as the "worst president ever". Another running gag has been headlining one especially egregious achievement, "And then they went to Elaine's." (Elaine's was a popular restaurant in New York City. It closed May 2011.)
Esquire did not publish "Dubious Achievement Awards" for 2001, but resumed them with the 2002 awards, published in the February 2003 issue.
"Dubious Achievement Awards" were discontinued in 2008, according to an editor's note in the January 2008 issue. However, after a nine-year hiatus, the feature was revived in the January 2017 issue with a skewering of 2016 events.
Sexiest Woman Alive
The annual Sexiest Woman Alive feature ran between 2003 and 2015, billed as a benchmark of female attractiveness.
Originally, it was a part of the "Women We Love" issue that had appeared yearly since 1988 (after being a section of "The Passions of Men" issue, June 1987), being initially titled "Woman of the Year". To build interest, the magazine would do a tease, releasing partial images of the woman in the issues preceding the November issue. By 2007, it had become the dominating story of the issue and to create an element of surprise the hints were abandoned.
Awards and honors
- In March, Esquire won a National Magazine Award for Digital Media—the first Mobile Edition prize—from the American Society of Magazine Editors.
- Winner for Profile Writing
- Winner for Personal Service, Feature Writing, and Leisure Interests
- Finalist for Profile Writing
- Finalist for Magazine Section
- Winner for Reporting
- Finalist for General Excellence (500,000 to 1,000,000 circulation), Magazine Section (two nominations), Feature Writing (two nominations), and Leisure Interests
- Winner for General Excellence (500,000 to 1,000,000 circulation) and Profile Writing
- Winner for Feature Writing
- Winner for Reviews & Criticism, Fiction, Design, and Profile Writing
- Winner for Reporting
- Winner for Reviews & Criticism
- Bulgaria (since 2014)
- China Shishang xiansheng (时尚先生) (since 1999)
- Colombia (2012 - 2017)
- Czech Republic
- Germany (1987-1992)
- El Salvador (since 2009)
- Hong Kong (published by SCMP Group)
- Indonesia (launched 2007, published by MRA Group)
- Italy (2018)
- Japan (launched 1987, published by Esquire Magazine Japan Co., Ltd.)
- Malaysia (launched April 2011)
- The Middle East (launched November 2009)
- Netherlands — Dutch: Nederland (from 1990) — ISSN 0926-8901, OCLC 73060315
- Philippines (launched October 2011, published by Summit Media)
- Poland (2015–2019)
- Republic of China (Taiwan)
- Serbia (launched October 2013, published by Attica Media Serbia)
- Singapore (launched September 2012)
- South Korea (launched November 2007, published by Kaya Media)
- Spain (from 2007) — ISSN 1888-1114, OCLC 436641278
- Ukraine (launched in March 2012, closed in 2014)
- United Kingdom (from 1991) — ISSN 0960-5150, OCLC 891154668
- Vietnam (launched April 2013)
- List of men's magazines
- Men's Health UK
- Esquire Network - A defunct television network based on the magazine
- Allegra Coleman
- Meyer Levin
- Nat Mags (UK publisher)
- Roberto Parada
- Yulia Spiridonova (Russian photographer)
- Levine, Jon (June 10, 2019). "Esquire Magazine Names Michael Sebastian Editor-in-Chief". www.wsj.com. Retrieved June 10, 2019.
- "eCirc for Consumer Magazines". Alliance for Audited Media. June 30, 2012. Archived from the original on January 23, 2017. Retrieved December 2, 2012.
- Bill Osgerby (Spring 2005). "The Bachelor Pad as Cultural Icon". Journal of Design History. 18 (1): 99–113. doi:10.1093/jdh/epi008. JSTOR 3527021.
- Mark Tungate (2008). Branded Male: Marketing to Men. Kogan Page Publishers. p. 120. ISBN 978-0-7494-5011-3. Retrieved March 14, 2016.
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- "Esquire". Encyclopædia Britannica.
- "Prologue: Selected Articles". archives.gov. March 8, 2012.
- Peterson, Theodore (1956). Magazines in the Twentieth Century. University of Illinois. pp. 260–262. OCLC 2770519. OL 6197440M.
- "Esquire | American magazine". Encyclopedia Britannica. Retrieved August 22, 2017.
- Carol Polsgrove, It Wasn't Pretty, Folks, But Didn't We Have Fun? Esquire in the Sixties (1995).
- Borgerson, Janet (2017). Designed for hi-fi living : the vinyl LP in midcentury America. Schroeder, Jonathan E., 1962. Cambridge, Massachusetts: MIT Press. pp. 269–280. ISBN 9780262036238. OCLC 958205262.
- "Normand Poirier". The New York Times. February 4, 1981
- Victor, Daniel (2016). "Editor of Esquire, David Granger, Steps Down". The New York Times. ISSN 0362-4331. Retrieved September 12, 2017.
- Tracy, Marc (May 23, 2019). "Esquire's Editor Is Out in Reshuffling at Hearst Magazines". The New York Times. ISSN 0362-4331. Retrieved September 23, 2019.
- "The Daily Endorsement - Thought of the Day - Things to Do When Bored". Esquire. Retrieved October 15, 2010.
- "David Granger: Why After 75 Years, Esquire Endorsed a Presidential Candidate". Huffingtonpost.com. October 9, 2008. Retrieved October 15, 2010.
- For a description of Lish's years at Esquire, see Carol Polsgrove, It Wasn't Pretty, Folks, But Didn't We Have Fun? Esquire in the Sixties (1995), pp. 239-249.
- The Wall Street Journal (February 25, 1977).
- Johnson, Adam. "Fiction". Esquire. Retrieved October 15, 2010.
- "Beautiful Women, Men's Fashion, Best Music, Drink Recipes". Esquire. Retrieved October 15, 2010.
- The New York Observer Archived October 18, 2008, at the Wayback Machine
- "Angelina Jolie, the Sexiest Woman Alive". Esquire. November 2004.
- Jacobs, A.J. (October 31, 2005). "Jessica Biel Is the Sexiest Woman Alive". Esquire. Archived from the original on June 17, 2010.
- Jones, Chris (October 31, 2006). "Scarlett Johansson Is the Sexiest Woman Alive - Scarlett Johansson Gallery". Esquire. Retrieved October 15, 2010.
- "Charlize Theron 'Sexiest Woman Alive' Esquire Magazine November 2007". Popcrunch.com. November 2007. Retrieved October 15, 2010.
- "Halle Berry "Sexiest Woman Alive" Esquire Magazine November 2008". Popcrunch.com. October 7, 2008. Retrieved October 15, 2010.
- McCammon, Ross (November 2012). "Mila Kunis Is the Sexiest Woman Alive 2012". Esquire. Cliff Watts (published April 16, 2013). Archived from the original on October 24, 2019. Retrieved October 24, 2019.
- "Esquire names Penelope Cruz 'sexiest woman alive'". sfgate.com. October 13, 2014. Retrieved October 13, 2014.
- Esquire, ed. (October 13, 2015). "Emilia Clarke Is the Sexiest Woman Alive 2015". Esquire. Archived from the original on October 24, 2019. Retrieved October 24, 2019.
- Markovits, Benjamin (October 13, 2015). "The Gorgeous Balance of Emilia Clarke, Sexiest Woman Alive 2015". Esquire. Archived from the original on June 27, 2019. Retrieved October 24, 2019.
- "American Society of Magazine Editors - National Magazine Awards Searchable Database". Magazine.org. Archived from the original on May 26, 2011. Retrieved October 15, 2010.
- Simon Dumenco. (March 29, 2011). "Esquire Editor David Granger on Esquire iPad App - Media - Advertising Age". adage.com.
- "时尚造就先生，先生定义时尚 - Esquire时尚先生网". hiesquire.com. Archived from the original on January 4, 2009.
- Esquire China Archived May 12, 2011, at the Wayback Machine
- Geng Song; Tracy K. Lee (July 2010). "Consumption, class formation and sexuality: Reading men's lifestyle magazines in China" (PDF). The China Journal (64). Retrieved August 13, 2015.
- Meike Werkmeister. (September 2003). Men's magazines in Germany Theory Head. Retrieved April 29, 2015.
- "Copyright Clearance Center: Esquire (155691917)". Copyright.com. Retrieved October 24, 2019.
- "Esquire gears up to become the ultimate guide for modern Filipino men". Summit Media. September 7, 2011. Retrieved October 6, 2011.
- "Attica Media - Naši magazini - Esquire". atticamedia.rs. Archived from the original on January 6, 2015. Retrieved January 6, 2015.
- "Copyright Clearance Center: Esquire (156622930)". Copyright.com. Retrieved October 24, 2019.
- "Esquire, National Geographic, Men's Health Magazines Closing in Ukraine". Sputnik News. November 16, 2014. Retrieved December 16, 2014.
- "Copyright Clearance Center: Esquire (123127551)". Copyright.com. Retrieved October 24, 2019.
- Official website (US)
- Official website (UK)
- Official website (Hong Kong)
- C Net News article about the experiment of the Esquire writer in Wikipedia
- "The Advertising Show: George Lois talks about creating Esquire covers". Advertising Age. November 5, 2005. Archived from the original (mp3) on October 13, 2006.