She began her artistic career creating pen and ink portraits of victims of the Great Depression, before proceeding to examine the struggles of the working poor in the towns of the Eastern United States through woodcuts, as well as producing drawings from the sit down strikes in Chicago.

Wealthy New Yorkers, the Milius' ancestors immigrated to the United States from Bavaria in the 19th-century and made fortunes in Manhattan real estate and textiles.

This upbringing led to Elsa Simonson socializing with modernist artists such as Charles Demuth, Marsden Hartley, Florine Stettheimer, and William and Marguerite Zorach.

From 1922 to 1932, Milius attended the Ethical Culture Fieldston School, which contradicted the views of her father by teaching racial equality, social justice and intellectual freedom.

[1] Elsa Simonson was an amateur painter, working out of a large art studio on Riverside Drive at which Winifred began her artistic explorations.

After an instructor told her to concentrate on plaster casts to bring "classic dignity" to her life drawings, she quit school and declared she was going to move out of New York.

[1][3] Disappointed with Grosz's lack of political energy, Milius began training under printmaker Harry Sternberg, who she described as a "spirited leftist".

Sternberg was a member of the John Reed Club, and his Marxist beliefs began to influence Milius and her fellow students including Rita Albers, Julien Alberts, Mary Annand, Hugh Miller.

Milius's works of the NYPL depict the buildings use as a shelter for Depression-era victims, reflective of the use of libraries today as an afternoon housing for the poor.

This piece, designed to bring public awareness to the plight of miners, was included in the American Artists' Congress "America Today" exhibition, which opened in thirty cities in December 1936.

The exhibition was designed to show awareness to social concerns and promote the ability to mass-produce prints in fast and inexpensive manners for wide distribution.

She befriended Mitchell Siporin, Morris Topchevsky, and Adrian Troy, joining them in their ongoing dispute against the Illinois Art Project (IAP).

Milius participated more than ever in the labor movement, and assisted Harry Sternberg in creating the painting Epoch of a Great City, when he came to Lakeview, Illinois to complete the mural at a post office.

Milius also became active in the Packinghouse Workers Organizing Committee, painting banners, creating illustrations for publications and disturbing those leaflets.

She also designed costumes for a musical called A Song About America, which depicted the Boston Tea Party, the Steel strike of 1919 and other revolutionary American moments.

Shortly after their marriage and move, they collaborated on their first book: Petticoat Picket Lines: The History of Women in the American Labor Movement, which Cecil Lubell wrote and Winifred Milius illustrated.

Milius continued to explore gender, race, and class through woodcuts based on historical motifs that depicted the lives of black women abolitionists.

During the Depression era, she participated in activities and events surrounding federal support for the arts, Congress of Industrial Organizations efforts to establish racially integrated labor unions, and the Loyalists opposition in the Spanish Civil War.

Following her death, the remainder of her children's book material was donated to the Kerlan Collection in Minnesota, and her artwork and wood blocks to the Rutgers University Libraries in New Brunswick, New Jersey.