The article analyzes literary texts and critical speeches of women and men-writers of the turn of the 19th – early 20th centuries, where the gender role models of the “new woman” and “superwoman” received the most vivid and original embodiment. Both models of femininity reflected the breaking of the usual gender order and the formation of a new system of values, in literature itself as well. The complex of feminist ideas associated with these types of models interested not only representatives of “high” literature. The creators of products for the mass reader, which absorbed both realistic traditions and the discoveries of modernism, also responded to the problem of women’s emancipation. N. M. Minsky in the play Alma and V. Bryusov in The Last Pages from the Diary of a Woman tried to present the model of the “superwoman” based on the Nietzschean vision. The field of activity for the “new woman” was outlined by E. A. Nagrodskaya and A. A. Verbitskaya in the novels The Wrath of Dionysus and The Keys of Happiness. Nevertheless, in all these works, the heroines failed, because they either became criminals, or faced an insuperable problem: actualizing the reproductive function or creative self-realization. Alma lost strength in the struggle for personal freedom, Bryusov’s Natalie became a murderer, Nagrodskaya’s Tatiana returned to the family shelter, Verbitskaya’s Manya, having achieved success in the art of ballet, committed suicide. And only M. Gorky in the novel Mother offered a solution: he put his Nilovna past the childbearing age and made her a freedom fighter for others. Thus, he managed to outline ways to rescue women from the snares of gender inequality. Nilovna can really be considered a “new woman”. And this utopian project turned out to be possible to implement in Soviet times by ignoring the real issues of gender controversies.