Lilian Westcott Hale (1880-1963) and her daughter Nancy Hale (1908-1988) built successful careers during a period of transition in America, as Victorian mores were replaced by new modern freedoms. Greater independence for women had evolved during the preceding century, before the influential cultural factors which occurred during the early twentieth century like urbanization and world war. This interdisciplinary analysis of Lilian Hale‘s artwork and Nancy Hale‘s writings demonstrates the imprint of the surrounding world on their work. Lilian Hale‘s art is influenced by her Victorian childhood, and Nancy Hale‘s fiction reveals many conflicts of the modern era. The study of these two women is enhanced by the wealth of primary documentation connecting their ideas and their lives to their artistic works. Both of the women ranked among the most respected in their fields during their lifetimes. Their works resonate with elements of their eras, demonstrating what it was to be a woman during the first half of the twentieth century. Lilian Westcott Hale and Nancy Hale both engage the gender constructs of their periods through their work. Lilian Westcott Hale‘s art is divided here into three distinct genres: her still lifes and landscapes express the confining environment the Victorian woman occupied; her idealized women reflect the period‘s taste for female perfection and beauty; her portraits and figure studies point to Hale‘s own distinction between males and females through their clothing and their poses. Unlike Lilian Westcott Hale, Nancy Hale demonstrates woman‘s new freedoms in an open manner, a result of the break with Victorianism. Hale‘s use of a literary medium allows her direct examination of the turmoil caused by the modern breakdown of Victorian structures. Lilian Westcott Hale refrains from harsh judgment of her daughter‘s world, while Nancy Hale‘s modern challenge of the previous era‘s standards leads her into troubling relationships and difficulties balancing her career with her personal life. Their work reveals the cultural ideologies of their respective eras and particularly the changes taking place for women.