During his many stays in Skagen, which from 1874 on had developed into a major artistic hub of Scandinavian painting, the Norwegian painter Christian Krohg focused on genre-like portraits and depictions of the basic lives of seafarers. Krohg had previously studied in Karlsruhe and Berlin and adopted a realistic manner of painting. In Paris in 1881, he was exposed to the work of Édouard Manet and to Impressionism under whose influence he adopted a brighter palette, which he subsequently managed to impart to the artists in Skagen.
The Portrait of a Fisher Boy Wearing a Southwester was created in Skagen in 1888. Standing in the right half of the canvas in three-quarter view, a boy wearing dark clothes and a southwester stares mutely at the viewer. Behind him are a grassy stretch of beach, a silhouette of rooftops and a bay. The landscape is overlaid with atmospheric cloud bands in light blue and yellow, hinting at the imminent sunset. Painted in soft pastel shades, nature contrasts with the dark figure of the boy whose melancholic expression is open to many interpretations.