In 1949, on his second day introducing himself to publishers in New York, Warhol received his first assignment as a commercial illustrator - to illustrate shoes for New York’s Glamour Magazine. His portfolio caught the eye of then-Art Director Tina Fredericks, who commissioned him on the spot to do work for the magazine. It was apparently at this job [after showing up for work with drawings of shoes that had been worn and looked a bit worn-out] that he learned a very important lesson: that shoes are the object of desire for every woman, and must therefore be presented in a favorable light. 

"One of Warhol's first jobs as a professional commercial graphic artist was to make drawings of shoes that were given to him. When he came back the next day with portraits of the shoes, Tina Fredericks, the art director of Glamour, explained to him that it was not about drawing the shoes with character, but about drawing new, unworn shoes. The shoes that served as his models began piling up at his apartment, and it is known that in these years his passion for shoe collecting emerged. The artist later wrote self-mockingly: 'When I used to do shoe drawings for the magazines I would get a certain amount for each shoe, so then I would count up my shoes to figure out how much I was going to get. I lived by the number of shoe drawings - when I counted them, I know how much money I had.'" (Adman, Warhol before Pop at page 101, footnotes omitted).

Warhol was also responsible for revamping I. Miller’s advertising campaign in the ‘50s, specifically through his blotted line drawings of shoes; he went on to produce more than 300 illustrations for I. Miller shoes, whose ads appeared in The New York Times almost every Sunday. He was so successful in this area that he eventually became known in the industry as “the shoe man”.