The earliest fashion photographs were made, probably in the 1850s and 1860s, to document fashion for Parisian fashion houses. Reproduction in fashion journals occurred much later, between 1881 (with the invention of the halftone printing process by Frederic Eugene Ives) and 1886 (when the refinement of the process made it financially practicable). This breakthrough made it possible to reproduce photographs and sell to a large audience through the medium of the printed page.

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 worl