In 1949, at the age of 20, Andy Warhol made the life-changing decision to move to New York City. Having just graduated from Pittsburgh’s Carnegie Institute of Technology—the predecessor of Carnegie Mellon University—with a degree in pictorial design, he could not have arrived at a more opportune time. His new home was the engine room of a rapidly evolving advertising industry centered on Madison Avenue.

Warhol took a playful and unusual approach in his commercial work that emphasized wit and creativity over technical ability. In doing so, he established his own identifiable brand—a whimsical illustration style that appealed to clients who favored the artistic values that it represented. Notably, his work privileged drawing at a time when photography was on the rise. Warhol established this approach with his first New York commission, for the September issue of Glamour magazine. By 1952, he had a roster of clients that included magazines, record labels, and the fashion industry.

During the 1950s, Warhol was especially renowned for his illustrations of shoes. In addition to receiving numerous advertising commissions from shoe manufacturers, Warhol often used shoes as the subjects of artworks. In 1956, in his first appearance in a museum exhibition, a shoe drawing was shown at the Museum of Modern Art.

Warhol’s largest body of commercial illustrations was produced for I. Miller & Sons, a shoe manufacturer and retailer that employed him to create large-format advertisements for The New York Times between March 1955 and December 1959. Lauded by the New York advertising industry, Warhol’s I. Miller campaign created an entirely new image for the company with innovative illustrations that often avoided directly representing the product being advertised. The company’s art director, Peter Palazzo, described Warhol’s advertisements as “full of good copy and ideas. We try to stir the woman’s imagination…to make her think of color without using color…to make her think of shoes without giving details.”

By the mid-1950s, Warhol’s success as a commercial illustrator had provided him with the means to embark on his first trip outside the United States. Accompanied by his friend, set designer Charles Lisanby, Warhol departed on June 16, 1956. Warhol documented the trip in a number of sketchbooks and collected many souvenirs along the way.

Warhol’s trip took him to San Francisco, Honolulu, Japan, Hong Kong, Manila, Jakarta, Bali, Singapore, Bangkok, Siem Reap, Colombo, Calcutta, Kathmandu, Benares, New Delhi, Agra, Aurangabad, Cairo, Luxor and Rome. Of particular note was his time in East Asia, where Warhol encountered extensive use of gold in traditional art and design. The trip may have inspired his use of gold leaf in drawings and for his book, A Gold Book (1957).

The years 1960 through 1962 were a period of transition for Warhol. He began recasting his persona from fey adman to cool artist and experimented with new ideas that ultimately paved the way for his first Pop works. Warhol executed his first concerted series of paintings and drawings at this time, taking the products of the advertising industry as his subject matter.

In many of his early Pop works, Warhol appropriated images from newspapers and magazines, platforms where his own commercial work was still regularly being published. He enlarged, cropped, and erased elements of the original images so that they no longer functioned as advertisements but were transformed into works of art.