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As early as 1898, Sarah S Stilwell was involved with book illustration; her first known book project was working with Ellen Olney Kirk (1842-1928) on Dorothy Deane: A Children’s Story with Illustrations (Boston: Houghton Mifflin and Company, 1898). Stilwell illustrated this fictional story about an eight-year-old girl named Dorothy Deane who boards with her grandmother and aunt after her father’s death while her mother works at a large school for girls in another town. Momma Deane is a “low priced teacher-of-all-work,” never having earned a diploma or degree. Dorothy, sheltered in an aloof New England household, makes friends with children in the neighborhood and they create their own world. The story conveys the fragility of American families at the turn-of-the-twentieth century.

In the frontispiece, Stilwell introduces the reader to Dorothy with her fair tresses cut shockingly short for contemporary fashion in a household where she is expected to become a modest and undemanding addition to the household. This is a powerful image that sets the tone for the story that is about to unfold: girls are not taught to be the center Dorothy sits near her Victorian grandmother who knits washcloths to be given with a bar of soap to needy children in the neighborhood (Dorothy does not realize and the time that she will be one to receive this gift). Dorothy befriends the neighborhood children that include eleven-year-old Marcia and ten-year-old twins Lucy and Gaynor. The next image (opposite page 62) shows the neighborhood children in Marcia’s kitchen as the group shares of feast of hot chocolate and toast in the absence of Marcia’s invalid mother (who remains in her bedroom) that allows them run of the house. The image sequence continues (opposite page 138) when Dorothy talks to a gardener; (opposite page 212) the gang explores the nearby woods and linger in a meadow; next (opposite page 280) they explore Marcia’s attic and dress up to play; the final image (opposite page 316) shows Dorothy “close in those loving arms” of her mother before she remarries. The text tells a very clear story: Momma Deane remarries a friend of her late husband not for romantic love, but to provide a home and opportunities for Dorothy.