Her career as a graphic illustrator was interrupted by 15 months spent entertaining the troops in World War I, which left her passionately anti-war.

While a student, she began her commercial art career drawing illustrations of hats for Gages, the largest millinery company in the United States.

She then moved to New York City, where she worked as a graphic artist and commercial illustrator, initially sharing a studio with Neysa McMein.

Between 1913 and 1929, her commercial graphics included covers for Saturday Evening Post, Colliers, Every Week, Fashion Art, McCalls, and Screenland; posters for the YMCA, and numerous advertising illustrations.

She worked in a canteen stationed with the American First Division army during the Second Battle of the Somme (1918) in March 1918, then in the Gondecourt sector.

[2] With artist Neysa McMein and Jane Bullard, she developed and performed a vaudeville show which toured the troops on the front lines.

She became known for creating the "New American Woman" image – idealized pictures of women who were young, beautiful, fashionable, invariably white and economically successful.

[5] In 1925, Willcox wrote a book called "Between Jobs and Babies", exploring the changing nature of women's roles in industrial society.

During the Depression, Willcox designed posters and graphics for Norman Thomas' League for Industrial Democracy, and for Masses magazine.

Conceived as a haven from racism, the Cold War, and McCarthy era red-baiting, Village Creek became the first interracial cooperative on the Eastern seaboard of the United States.

[11] In 1952 Anita and Henry Willcox represented the Quakers at the Asia and Pacific Rim Peace Conference in Peking China.

[13] (During the 1950s, when Robeson was unable to perform in public venues, he practiced on the piano in the Willcox house in West Greenwich.)

At aged 70, she was called to testify before Eastland Committee (both for attending the China conference, and as the person who funded the legal defence of Harvey Matusow, an FBI informer jailed for publicly admitting perjury as a state witness against "communist" trade union officials).