During the Joseon Dynasty (1392–1897), many silk portraits were made of kings and other public officials. Most of these are now lost. Silk canvases are partially transparent, which allows pigments on both sides of the canvas to be seen. Before working with a silk canvas, artists would create several drafts of their portraits on paper, which was made translucent through the application of oil. In this research, a set of three paper drafts for a portrait from the eighteenth century was analysed via X-ray fluorescence spectroscopic data and microscopic imagery to identify the type of paper and pigments used. Using this analysis, along with surviving historic records, comparisons to other historic portraits, and an artistic analysis of the line and colouring techniques, new insights into the process of making these portraits are presented. Novel features of the three sketches are identified. Furthermore, the step-by-step process used to create these sketches is discussed and illustrated using a reproduction that employs traditional techniques and materials.