Medieval cities were more than centers of trade and governance—they were imagined, shaped, and contested through literature. This project examines how Bruges, Ghent, and Ypres were represented in Middle Dutch and Middle French texts (14th–15th c.), revealing how urban representation reflected social structures, political tensions, and cultural ideals. While historians and archaeologists reconstruct material realities, literary portrayals remain understudied. Integrating literary analysis with historical, linguistic, and archaeological perspectives, this study shows how medieval texts shaped urban identity. By analyzing historiographies, hagiographies, allegorical poetry, and technical literature, it employs a three-tiered methodology: macro-level manuscript analysis (audience, transmission, context), micro-level textual analysis (urban descriptions across nine themes), and a comparative approach mapping patterns across genres. A key focus is the multilingual interplay between Middle Dutch and Middle French, revealing how language shaped urban identity. Comparing texts with historical maps, archaeological records, and urban iconography, this study challenges static views of medieval cities, showing that representations of Bruges, Ghent, and Ypres were deeply ideological, reflecting anxieties about power, economy, and civic belonging. By bridging literary and historical urban studies, it redefines the medieval city as a constructed, contested, and symbolic world.