Penn studied at the Philadelphia Museum School of Industrial Art (1934-1938). Alexey Brodovitch, art director of Harper's Bazaar, whose design seminars Penn attended, introduced him to fashion magazines; moreover, he hired Penn to be his assistant during two summers. Brodovitch published some of Penn's illustrations in 1937. In the same year, Penn undertook a series of street photographs of the shop signs and facades of New York, where he was laying the groundwork for a career in the fashion world by working as a freelance graphic designer and consultant art director for Saks Fifth Avenue.
By 1942, having spent a year painting in Mexico, Penn recognized that his future lay elsewhere. In 1943 Liberman hired him as a creative assistant in the art department of Vogue. Penn found Vogue's photographers mostly ambivalent about his ideas for the magazine's cover artwork and instead put them into practice himself. His first Vogue cover, a still life composition of accessories, was published in October 1943. Over the next sixty years he photographed nearly 170 more. Shortly after his 1943 debut, he embarked on the photography of clothes. He followed this with a short-lived but inventive series, Portraits with Symbols, a stylish fusion of still life and portraiture in which well-known figures posed with objects that evoked aspects of their personalities.
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