Winsloe led a life in opposition to the expectations of her family and her society and created from it a body of fiction that portrays the difficulties felt by a woman who does not wish to conform. Her role was to have been that of an army officer's wife; instead, she pursued a career as a sculptress. In 1913, however, she did fulfill her family's desire by marrying the Hungarian Baron Ludwig Hatvany.

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Her first literary effort, Das schwarze Schaf (The Black Sheep), dates from the early years of her marriage. The unpublished novel portrays a girl who is a social outsider, both at school and in her career as an artist. She gains acceptance only through marriage to the right man.

Her real life took a different turn. Owing to her husband's numerous affairs, Winsloe went to Munich where she returned to sculpting and also began to write professionally.

Her novella Männer kehren heim (Men Return Home; date unknown) voices the concern that would motivate her fiction, namely, the question of sexual identity within a society stratified according to gender roles. During World War I, a girl is attacked by several soldiers and, to maintain her safety, she dresses in her brother's clothes for the rest of the war.

In 1930, her drama, Ritter Nérestan (Knight Nérestan), premiered in Leipzig. Retitled Gestern und heute (Yesterday and Today) for its Berlin premiere, this play made Winsloe's career as an author. The work became most famous in its film adaptation, Mädchen in Uniform (Girls in Uniform; 1931, directed by Leontine Sagan).

The play tells of the schoolgirl Manuela von Meinhardis, who is forced into the strict confines of a Prussian girls' school. She finds solace and love in her relationship with one of her teachers, Fräulein von Bernburg. After performing the lead male role in the school play, Manuela has too much to drink and openly declares her love for her teacher.

The headmistress views such feelings as "sinful" and "morbid" and decides Manuela must be expelled. Unable to face separation from her beloved, Manuela commits suicide. Two conclusions were created for the film version. In one, Manuela dies, but in the other she is saved by her classmates. The latter version was deemed unacceptable by American censors; therefore, the former was for decades the only version available in the United States.

Winsloe was involved in a lesbian relationship with the American journalist Dorothy Thompson in the early 1930s, but it ended by 1935. Thompson seems to have been uncomfortable with living as or identifying herself as a lesbian, and Winsloe could not find work in the United States.

Winsloe's novel Life Begins (1935), published only in English, describes a young sculptress who gains the courage to live openly with the woman she loves. The heroine of her last novel, Passagiera (Passengers; 1938), however, has lost that confidence. Her identity as a woman and even as an individual disappears as she submerges herself in the mass of people on board an ocean liner.

Winsloe continued writing, turning to film scripts. One of these films, Aiono (1943) returns to her earlier theme by depicting a Finnish refugee who dresses in male clothing in order to survive.

Winsloe was active in the antifascist movement in France, even hiding refugees in the home she shared with her lover, the Swiss author Simone Gentet. Under circumstances that have never been completely clarified, both women were murdered in early June 1944.

Since the 1960s, European film has included significant gay-themed films, many of them directed by openly gay and lesbian directors.

The contributions of gay men and lesbians to twentieth-century French literature have been closely intertwined with the course of mainstream literature.

With major periodic setbacks, over the last two centuries German-speaking authors have gradually developed a gay and lesbian positive literature.