Jan De Maesschalck's paintings represent a sharp view on topical subjects and the news. However, his clear observation of current events is depicted within an atmosphere of muse and memory. As such, his work represents an impression of melancholy and mockery, yet both in a mild form. His subjects relate to an impression of intimacy and loneliness, but the mood is never harrowing or heavy. According to De Maesschalck, melancholy leads to beauty. The tone set in the depiction of schadowy interiors and forlorn women is relativising and even humorous. All works speak of a strong but indefinable desire. The paintings are tender riddles.

De Maesschalck's metier reveals an extreme attention for detail. With technical precision, he prepares his paper and draws with paint. Utilising acrylic paint that dries immediately, De Maesschalck has to work fast. At the same time, the chosen method enables him to differentiate techniques and materials during the creative process. He is both a drawer and painter. Brushstrokes are visible, and hence his secure draughtsmanship contributes to the vibrant quality of the works.