Jacobus Van Looy was born on 12 September 1855 in Haarlem as the son of a carpenter. His father lost his job when his eyesight began to fail. His mother died when he was five years old. When his father died soon afterwards, Van Looy ended up in the local orphanage, now the Frans Hals Museum. He trained to become a house painter, but was able to follow drawing classes from 1877 on at the Art Academy in Amsterdam. In 1884, Van Looy received the Prix de Rome, which allowed him to travel. The following two years he spent traveling through Italy, Spain and Morocco. Until 1894 he lived in Amsterdam, when he married Titia van Gelder and moved to Soest. In 1901, the couple traveled to Spain and Morocco. Van Looy moved back to Haarlem in 1913. After his death in 1930, his house at the Haarlemmerhout Park was converted to a museum in his name, although it closed in 1976 and the collection transferred to the Frans Hals Museum.

The Rijksakademie, founded in 1870, was a classical art academy and home of the Amsterdam Impressionists. In 1880, August Allebé became its director, who left a mark on the next generation of attending artists. His cosmopolitan attitude veering towards the avant-garde attracted talents such as George Breitner, Jan Toorop, Piet Mondriaan, and Willem Witsen. Witsen and Van Looy became friends at the Academy and were at the center of the Tachtigers or Movement of Eighty, a radical group of writers and artists active around the year 1880. The Eightiers believed that style must match content. Van Looy’s prominence rose as a writer, whereas he used his art predominantly for his personal pleasure: producing portraits of acquaintances and his beloved garden.