Lisa Stillman grew up in the heady atmosphere of Pre-Raphaelitism. Her father, William J Stillman, was dubbed 'America's first Pre-Raphaelite painter', and produced intensely detailed landscapes until about 1860, when he stopped painting in response to critical interference from his friend John Ruskin. He then concentrated on journalism and photography, while also acting as American Consul, first in Rome, and later in Crete and Athens. His diplomatic career ended in 1870, when his first wife committed suicide, as the result of the stresses of Greco-Turkish war. He left Greece with his three children, including Lisa, and settled in London, where he was supported by both the Rossetti family and members of the capital's Greek community. In April 1871, he married Marie Spartali, an aspiring painter of Greek descent, who studied under Ford Madox Brown, and modelled for Dante Gabriel Rossetti.
Through the 1870s and 1880s, Lisa Stillman lived mostly with her family in Italy, where her father was foreign correspondent for the London Times and leading American newspapers. She developed as a portrait painter in a Pre-Raphaelite vein inspired by the example of her stepmother, and exhibited her work from 1888 at such leading London venues as the Royal Academy, the Royal Society of Portrait Painters and, especially, the New Gallery. Following the death of her father in 1901, she continued to live with her stepmother and siblings, including her sister, Effie Stillman, who worked as a sculptor and medallionist.
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