Henry Wolf, who died Monday at his Manhattan carriage house at age 79, was one of the seminal magazine designers of the 1950s and 1960s, with his bold and often humorous art direction for Esquire, Harper’s Bazaar, and Show.

He later moved into advertising as a photographer and eventually owner of an agency, where he produced arresting campaigns for such clients as Xerox, Saks, and Van Cleef & Arpels, and helped invent the magazine-style product catalog.

For a typically droll Esquire cover from July 1958, pegged to an article titled “The Americanization of Paris,” Wolf portrayed a packet of powder marked “Instant Vin Rouge” being poured into a wine glass. “I combined France’s passion for red wine with the U.S.A.’s predilection for fast (or ‘instant’) food,” Wolf wrote in his book “Visual Thinking.” “Esquire got hundreds of letters asking where this fictitious product could be purchased.” Another magazine cover depicted Esquire’s trademark – an ogling playboy – constructed of wire backing in a chair that supported a shapely female posterior.

Wolf replaced the legendary Alexey Brodovitch as art director at Bazaar in 1958, and while the covers he produced were necessarily less louche, they were no less creative, often combining typography as a design element in novel ways. A Richard Avedon photograph on the December 1959 cover shows a pink caped model precariously balanced on a ladder, hoisting the penultimate ‘A’ into the Bazaar masthead.

Wolf’s own artistic inspirations were less about couture than the Expressionist and Surrealist art of his native Austria. Bazaar’s editor, Diane Vreeland, “tried to incorporate me into the fashion world, but to this day I don’t understand it too well,” Wolf wrote in 1988. “Mrs. Vreeland considered that shortcoming an asset.”

Born in Vienna, Wolf was raised in a prosperous secular Jewish family that owned several carpet factories. Just 13 at the Anschluss, he fled with his family through France and detention camps in Morocco, where Wolf contracted malaria. They finally made it to New York in 1941. His father found work as a furrier, but the family fortune had vanished with the war.

Wolf attended the School of Industrial Arts before being drafted into the Army in 1943. After being stationed in Leyte and Luzon, he became part of the Japanese occupation just weeks after Hiroshima. “The four months I spent there were some of the happiest of my life,” he wrote. “There was a strange country to be explored, and the wonderful expectation of returning to New York.”

When he finally did return, Wolf found work at an advertising agency and then, in 1952, at Esquire, where he started as a designer and quickly became art director. At Esquire, Wolf instituted a thoroughgoing redesign, integrating article content with page layout in a sophisticated and playful way. In a valedictory when Wolf left for Bazaar, Esquire’s founder and editor, Arnold Gingrich, wrote: “I don’t say that nobody else could have done this. I simply say that, in the twenty-five years of this magazine, which began when Henry Wolf was an eight-year-old in Vienna, nobody else has.”

At Esquire, Bazaar, and Show, Wolf discovered or worked with any number of young rising talents. Robert Benton – Wolf’s first assistant at Esquire and much later a screenwriter and director on “Bonnie and Clyde” and “Kramer vs. Kramer” – told The New York Sun that Wolf was “the most opinionated person I have ever seen, but with great judgment.”

Wolf more or less discovered the photographer Melvin Sokolsky, whom he set to shooting Bazaar covers at age 21.Wolf was an early supporter of Saul Leiter and Milton Glaser, and taught Jill Krementz, then a writer for Show, how to load a camera. He was less fond of Diane Arbus and told the New York Times, “Once I ran into her on a beautiful Saturday morning all decked out in her cameras. ‘What are you doing on such a gorgeous day?’ I asked. ‘Trying to find some unhappy people,’ she answered. Well, I couldn’t relate to that!” Despite Arbus’s repeated entreaties, Wolf refused to publish her photo of the human pincushion.

In 1965, “having run out of magazines,” he wrote, Wolf partnered with Jane Trahey to form an advertising agency. Celebrity campaigns were among their specialties, often shot with Wolf behind the camera. One series for the typewriter company Olivetti depicted “Duke Ellington at the Keyboard.” As payment, Ellington requested 100 typewriters be sent to his boyhood school. The agency also began the long-running (still-running) “What Becomes a Legend Most” campaign, in which female celebrities are photographed wearing Blackglama minks.

He founded Henry Wolf Productions in 1971 and was soon producing magazine-like catalogs for Saks. Among his more memorable images from this period is an ad featuring a Roman numeral clock perfectly superimposed on a model’s face, the implication being that Revlon can ameliorate the aging process. He did design and photography work for many large corporations, including IBM, GTE, and Westvaco. He also created the credits for most of Mr. Benton’s films.

In 1988, Wolf published “Visual Thinking,” a lavishly produced volume that lays out in images – and mercifully little text – his design principles under chapter titles such as “Unexpected Combinations,” “Repitition,” “Humor,” and “Improbable Settings.” As an example of the latter, he included a fashion ad for a woman seemingly walking on water. She was, he disclosed, actually being supported from below by a frogman.

Ever the man-about-town and bon vivant, Wolf indulged his tastes for women and fine automobiles. He stored his Rolls and his Alfa Romeo in the garage of his East Side carriage house and maintained a country estate in North Salem. He was linked to a succession of beautiful women, not least his two wives and the actress Ali McGraw, whom he met when she was Alice McGraw and an assistant to Vreeland.

He liked to tell friends he hadn’t read a book since World War II, and often told a joke he said originated at Sunday dinner in Vienna: “Your date is beautiful, but dumb,” his father told Wolf’s uncle. “No, she is beautiful, and dumb,” the uncle countered. Of his own preferences, Wolf wrote, “Renata,” his first wife, “was beautiful – which I understood; and intellectual – which I understood less.”

His privately published memoir was titled “Hopeless But Not Serious,” a favorite saying that hinted, perhaps, at the melancholy friends detected as he approached old age.

In 1954, Cooper Union hired Wolf as an instructor, having previously rejected him for lacking the proper credentials. Later, he taught at the School of Visual Arts and at Parsons, which he generously supported and which granted him an honorary degree.

In 2003, Sotheby’s presented an exhibit of Wolf’s designs, as well as the Surrealism-influenced painting he took up in his later years.

He was modest about his own originality. “You swipe from many sources and the combination of the sources evolves a style for yourself,” he once told Print magazine. “Paul Rand swiped from Paul Klee and I swipe from Paul Rand and yet Rand doesn’t look like Klee and I hope, sometimes, I don’t look like Rand, because I also swipe from others.”

Henry Wolf

Born May 23, 1925, at Vienna, Austria; died February 14 of natural causes at his Manhattan home; survived by a sister, Joan Slawson.