Helen Hokinson studied at the Academy of Fine Arts (today the School of the Art Institute of Chicago). She was first employed as a fashion illustrator for department store Marshall Fields. In 1920, Hokinson moved to New York City and became a cartoonist. Her cartoons first appeared in The New Yorker in 1925. By the time of her death, she produced 68 covers and more than 1,800 cartoons for the magazine.