Andy Warhol left Pennsylvania for New York in 1949 to become a commercial illustrator. Upon arriving in New York, he quickly realized that photography was putting many commercial illustrators out of business. Warhol adapted to this reality by incorporating photography into many of his works into the 1950s – he would photograph his subjects and then trace over the photos, incorporating his own techniques and whimsical additions into the drawings (Schleif, 11). His interest in photography was intensified by his encounters and later friendship with Otto Fenn; the two met in 1951 and Warhol became a regular at Fenn’s photography studio, which is said to have attracted gay creative minds of New York in the 40s and 50s. Warhol helped Fenn with the backdrops for his photography shoots; Fenn’s photographs – often of men in drag – became the foundations for many of Warhol’s early drawings. 

This drawing is similar to the illustrations that appeared in Warhol’s unpublished (and unfinished) book, Ladies’ Alphabet (1953). Imagery in that book (and in many of the books he published in the 1950s) originated from two primary fonts: history (especially antiquarian books and the New York Public Library’s Picture Collection) and pop culture, such as contemporary life magazines and movie star photos (Wrbican, 64). In the case of Ladies’ Alphabet, the subjects are based on the aforementioned photos of movie stars and pop culture icons (50), or on photographs that he and Otto Fenn took of men in drag (Schleif, 8).

References:
Schleif, Nina. Drag & Draw: Andy Warhol, the Unknown Fifties. Munich: Hirmer, 2018. Print.
Wrbican, Matt. "Adman: Warhol before Pop." Adman: Warhol before Pop. By Nicholas Chambers. Sydney, Australia: Art Gallery NSW, 2017. 67+. Print.