This dissertation traces the history of the objects, craft knowledge, and practices of artisan tailoring on the Abomey Plateau in central Benin (former Dahomey) from the pre-colonial era to the present. It begins with a survey of cloth and clothing production and consumption in the slave-trading Kingdom of Dahomey (c.1600-1894) when most men and women wore wrapped or draped cloth and few sported tailored outfits. Wrapping remained the primary mode of dress long into the era of French rule (1894-1960), despite colonial programs to regulate clothing production through controls on artisan labor and the growing popularity of styles such as dresses, skirts, trousers, and suits. My project then traces the rise of tailoring and the increased demand for fitted clothing in the post-WWII era to the present. Tailoring fostered new possibilities for men and women and their respective gender roles, while the process of clothes-making in central markets and neighborhood workshops helped to materialize urban spaces and ideas about city life. At the same time, the advent of tailoring apprenticeships served as an alternative to formal education and opened new professional pathways to both men and women. By revealing this long history of shifting sartorial practices of production and consumption, I show how ordinary Beninois men and women experienced and gave meaning to modernity, urbanization, and political transformation. I argue that tailors and artisan-made tailored clothing helped Beninois make sense of political and social changes. As new independent states emerged in the wake of colonialism and as the region urbanized in the mid-twentieth century, tailored fitted clothing served as a site where ordinary people worked out what it meant to be part of a new nation and a new city. By producing clothing for clients, tailors played a key role in leading conversations with their fellow citizens about how men and women should look and act in an independent and modern Benin. Indeed, I argue that by designing, cutting, and sewing fitted clothes, tailors materialized and gave expression to new possibilities of self, city, and nation during this tumultuous period in West African History.