This article contextualizes the visual intrigue that was created by the fifteenth-century Chinese poet and painter Sun Ai (ca. 1452–1536) when he broke from convention by using indigo blue to color the leaves of a cotton plant and a mulberry branch in a pair of paintings now in the Palace Museum, Beijing. The key to the meaning of this unique coloration lies in the poems inscribed by Shen Zhou (1427–1509) and Qian Renfu (1446–1526), as well as the socioeconomic connotations of silk, cotton, and indigo in those scholars' regions. It is argued that these paintings were made shortly after the Hongzhi emperor (r. 1487–1505) banned the submission of multicolored cotton and silk textiles. Considered in that context, the monochromatic use of indigo not only alluded to what cotton fibers and silkworms would ultimately produce—cloth and silk to be dyed indigo—but also stood in stark contrast to the kaleidoscopic appearance of the clothing banned by Hongzhi. The collaboration between Shen Zhou and Qian Renfu makes the paintings prominent examples of the layered nuance achieved in traditional Chinese painting through the interplay of color and poetry.