In the centuries leading to the Counter-Reformation in Italy, literature and art were platforms in which the Church could be criticized and redefined. This paper explores the imagery of Mary in art and literature from Dante until the Council of Trent, demonstrating how she transformed from solely a religious icon to an all-encompassing cultural figure present in art, literature, politics, war, and questions of morality. It focuses on her importance not only in public ritual, but in physical spaces of Italy, inciting discomfort at the display of her gendered body. Initially poets like Dante reacted by comparing Mary to their beloved in order to draw themselves closer to God, emphasizing her beauty as reflective of the divine. As the violence in Italy intensified, this was reflected in Mary’s portrayal as she was increasingly depicted as a suffering mother. Women in the Counter-Reformation incorporated the use of Mary’s affect in their poetry, reflecting on the purpose of female suffering in a society of escalating conflict and factionalism.