Helen was the daughter of Adolph and Mary Hokinson. Her father was a farm machinery salesman and her mother was the daughter of the well-known lecturer, Phineas Wilcox, known as the Carpenter Orator.
Helen Hokinson graduated from Mendota High School in 1913. Two sketchbooks from her high school years are on display at the Hume-Carnegie Museum. She studied art in Chicago at the Academy of Fine Arts and began drawing fashion illustrations for department stores including Marshall Fields. From Chicago she went to New York where she continued her studies, did fashion illustrations and tried cartooning with a comic strip which failed.
The New Yorker was founded in 1925 and Helen submitted one of her drawings to the editors. She stopped back two weeks later and learned her drawing had been accepted. She was asked to continue sending drawings each week for possible publication. It is said that 1,700 Hokinson cartoons were printed.
In 1931, Miss Hokinson met James Reid Parker with whom she formed a business relationship. She created the drawings, he wrote the captions.
From 1925 until her death on November 1, 1949, her drawings regularly graced the pages of The New Yorker. She and Parker did a monthly panel called "The Dear Man" for Ladies Home Journal. They also worked together on some advertising jobs.
Her drawings for The New Yorker featured plump well-to-do club women who wore high heeled shoes and were conscious of hats, fashions, caring for pets, and gardens. After a time she became fearful people were laughing at rather than with the buxom, strong minded but occasionally befuddled women whom she had stamped as her own, and launched a crusade to defend and explain them.
Helen Hokinson published several books of her own cartoons: So You're Going to Buy a Book in 1931, My Best Girls in 1941, and in 1948 her last book, When Were You Built? The Hokinson estate published: The Ladies, God Bless Them in 1950, There Are Ladies Present in 1952, and The Hokinson Festival in 1956.