This dissertation examines notions of modesty in behavior and appearance as represented in romance and conduct literature of the German Middle Ages. I look to the Winsbecke poems and Thomasin von Zirclaria's Der Welsche Gast as representative samples of conduct literature, considering them alongside the four core courtly romances: Hartman von Aue's Iwein and Erec, Gottfried von Strassburg's Tristan, and Wolfram von Eschenbach's Parzival. The project is guided by four central areas of inquiry. First, I investigate the "cleavage" between the two genres of romance and conduct literature, exploring the ways in which they cling to each other as reference points and split off from the other's constructs. Second, I pay close attention to gender differences in the practice of modesty, investigating precisely what they are and how they structure gender roles and courtly identity. My third area of emphasis traces the ways in which sight and the body engage with notions of modesty. Finally, I examine the relevant changes the German romance authors make to their French source material. My analysis relies on three primary keywords in locating medieval modesty (zuht, kiusch, and scham), and explores the intersections between scham "shame" and scham "modesty." I show that, compared to the French originals, the German romances demonstrate a far greater interest in the display of the naked or partially naked body. These scenes, which appear with regularity, follow particular patterns according to gender: for example, a naked man is uncourtly, but a partially-naked woman has a high status. Gender is also a determining factor in the overall importance of modesty, particularly as seen in conduct literature: for a man, it is one of several critical components for knightly success, while for a woman, it provides the fundamental structure for her life. I also find unexpected complexities in the relationship between romance and conduct literature. Each genre has its distinct areas of permissiveness and regulation with regard to modest behavior.