The colonial city of Riobamba was founded in 1534 in what is now Ecuador. The city was a major textile center and provided trade between other cities and missionary settlements throughout the Andes. In 1797, a devastating earthquake hit the region. A large percentage of the population was killed and much of the city was destroyed or covered in silt. Following the disaster, survivors were forced to move 16 kilometers away where they established the modern city of Riobamba. This study examines life and identity in colonial Riobamba prior to this catastrophe. Interdisciplinary methods are employed in an examination of two separate religious orders that resided in Riobamba between the years 1645 and 1797. I carried out this work through archaeological excavation and archival study of historical documents. Over the course of this project, the two monasteries were extensively surveyed and thirteen units were excavated. The following research reveals the close connection between common material culture recovered from within these monasteries and the identities of the men who routinely used these items. Traditional understandings of colonial masculinity describe gendered behaviors as rigidly defined. My research however, demonstrates that gender expectations were somewhat flexible and adapted both to the environment and the immediate needs of the group as a result male gender is expressed as multiple masculinities. This study shows that monastic men occupied a range of gendered roles while maintaining positions of relative power within the community. This multiplicity of identities troubles our current understanding of masculine behaviors and identities within this particular context.