Jessie Aitken Wilson was the sister and secretary of physician, chemist, and Regius Professor of Technology, George Wilson (1818-1859), who was also the first Director of the Industrial Museum of Scotland. Both were siblings of the anthropologist Sir Daniel Wilson (1816-1892). Another Wilson sister, Jeannie Wilson, married Frank Oliphant, the brother of the novelist Mrs. Oliphant (1828-1897). Archibald Wilson (1784–1843), a wine merchant from Argyll, and his wife, Janet Aitken, were the parents of Daniel, George (and a dead twin brother), Jeannie, and Jessie.

On 6 October 1865, in her mid-life, Jessie Aitken Wilson married the much younger writer, James Sime (1843-1895). Their daughter would become the novelist Jessie Georgina Sime (1868-1958).

In 1866, having given up the idea of entering the ministry, James Sime went to Germany, to study German literature and philosophy, first at Heidelberg University, and afterwards at Berlin. During his stay in Germany he collected materials for his Life of Lessing, and he visited most of the places connected with his hero and with Goethe and Schiller. On his return from Germany he settled in Notting Hill, London, in 1869, and began journalism. In 1871 he joined the staff of the Edinburgh Academy but, finding the work uncongenial, resigned and returned to London in 1873 to write. Both his wife, Jessie Aitken Wilson Sime, and his daughter, Jessie Georgina Sime, survived him.

Jessie Georgina Sime moved to Montreal in 1907 and soon became involved in the city's literary and intellectual community. In her fiction and non-fiction, Sime was an early modernist and realist, and directed her attention to the social, economic, and emotional difficulties of working-class women and the urban poor. Her fiction includes Sister woman (1919) and Our little life: a novel of today (1921) the latter of which was reprinted in 1994 with an introduction by K. Jane Watt.

Frank Nicholson, Edinburgh University Librarian and a long-time friend and writing partner of Jessie Georgina Sime, and eventually too, his widow, Mary Nicholson, became custodians of Sime's material which included family keepsakes.