Renaissance portraiture represents more than the sitters. These images portray complex conceptualizations of identities, layered amalgams of the personal and political; dynastic and economic; amorous and pious; and present, future, and eternal. In the late fifteenth century, side profile portraits were the norm, characterized by the superiority of aloofness and nonchalance. Typically commissioned by husbands to celebrate marriages, these portraits memorialize the brides’ domesticity, piety, and above all, chastity. With Leonardo da Vinci’s groundbreaking Mona Lisa of ca. 1503 came the revolutionary change in female portrait composition, widely imitated by masters of the time. Females portrayed after this transition engaged the viewers directly, deviating from the previous detachment. These portraits are focused on harmony, with the prevalence of triangular formations along with scenic backdrops. The early sixteenth century saw another shift in female portrait ideals: artists were no longer constrained by traditional female decorum, but rather focused on exploring feminine sexuality. Belle Donne paintings and various counterparts grant viewers intimate insights into the lives of Renaissance women, whose sexuality was celebrated in the private sphere but remained taboo in public. Eventually, as more female art patrons rose to power in the mid-sixteenth century, the practice of female portraiture ceased to be dominated by male patriarchy, becoming rather a part of the female sphere. In this paper, I explored the evolution of female portraiture in chronological order, tracing the shift in feminine decorum along the way, ending with a survey of the connection between the art world and the literary realm.