Jan Toorop was born in Purworejo on the island of Java, as the son of a half-Chinese mother and a father who clerked for the Dutch colonial government that ruled the Indonesian archipelago during the nineteenth century. Descendants from Belanda Hitam (Black Dutchmen), Africans recruited from the Dutch Gold Coast to service as colonial troops in the Dutch East Indies, the young Toorop was certainly considered exotic at the time he moved to The Netherlands in 1869. Enrolled in 1880 at the Rijksacademie in Amsterdam, the conservative outlook of the academic painters was not much of interest to Toorop. By 1883, Toorop befriended the Belgian artist William Degouve de Nuncques, who introduced him to the avantgarde in Belgium.

For Toorop, European culture became an addition to the foundation he had been exposed to as a child in Indonesia. Like Vincent Van Gogh, Toorop became a socialist sympathizer after observing the people at work in the slag heaps of the Borinage, a horrific landscape more vivid than any hell imagined by the Symbolists. Poetry by Maurice Maeterlinck and Emil Verhaeren became the source of inspiration for Toorop and his contemporaries. From 1882 through 1889, Toorop lived intermittently in Ixelles, near Brussels. Joining the newly formed Lex XX (Les Vingt) in 1884, he was immediately part of the inner circle of the “revolutionaries”: James Ensor and Fernand Khnopff. As the sole Dutch member of Les XX, Toorop forged important relationships between his peers in Belgium and The Netherlands. After meeting the British student Annie Hall (1860-1929) in Brussels, Toorop split his time between The Netherlands, England and Belgium. In April 1890, the couple settled in the Dutch coastal town Katwijk aan Zee, jumpstarting a new artistic endeavor. Notwithstanding an absence from Holland for nearly a decade, Toorop was considered the most important Dutch avant-garde artist at the time, with international connections and aspirations.

Soon after returning to the Netherlands, Toorop cofounded the Haagse Kunstkring, where he organized the first retrospective exhibition of Vincent van Gogh, followed by a group show of Les XX in 1892. That same year, Sar Péladan visited The Netherlands, luring Toorop to join his Salon de la Rose+Croix and ushering in his foray into symbolism. Soon, seductive, fatal women, symbols of sensuality and destroyer of man, entered Toorop’s emblematic vocabulary. Embracing his colonial East Indies heritage of tropical vegetation, carvings and Hindu iconography, Toorop began his most important symbolist drawing The Three Brides, now in the Kröller-Müller Museum, Otterlo. After its completion in 1893, Toorop returned to portraiture, employing his personal symbolism: the soul is revealed in a fantasy, embodying different types of beings rather than the formality of a portrait. The sitter no longer represents a particular woman, but rather the embodiment of a melancholic mood.

Like his symbolist contemporaries, Toorop sometimes situated his work in Bruges, a medieval town in Belgium. The mystic aura of fifteenth century architecture and paintings by the Flemish primitives such as Rogier van der Weyden and Hans Memling appealed to the fin de siècle artists. Bruges is seemingly a second sitter in Toorop’s present drawing and the slightly larger drawing in the Kröller-Müller Museum, both dated 1915. Rather than a formal portrait depicting a sitter, the artist’s archetypal muse seems to appear. Toorop’s daughter, Charley, was the artist’s preferred model until 1912, when their relationship became fraught when she married the philosopher Henk Fernhout. That same year, she was replaced by Miek Janssen, his future favorite model. The downward gaze and symmetrical frontality of the sitter are typical for Toorop during this period, as is the allegorical appearance of Bruges. The arched bridges, inspired by the Begijnhof, are also a well-known motif known from Fernand Khnopff’s 1892 frontispiece for Bruges-la-Mort by Georges Rodenbach.