The portrait bust of Vittoria della Tolfa Orsini (d. August/September 1586) occupies the central niche of her funerary monument, opposite that of her husband, in the chapel she erected in Santa Maria in Aracoeli, Rome. Visual and documentary evidence challenges the assumption that the chapel’s ensemble, and the portrait in particular, realized the donor’s intentions. Indeed, the bust was likely a late addition arranged by Orsini’s heir. The portrait’s gaunt face has been regarded as unsparingly frank. Yet, sixteenth-century portrait theory and prescriptive texts on women’s behavior support an emblematic reading of the advanced age seen in the portrait. The physiognomy, costume, and gestures all contribute to an image of a virtuous elderly widow, a paradigm current in the post-Tridentine era. Embedded in a consecrated chapel, the portrait perpetuated the memory of Orsini in an ideal and enduring form and offered a model of piety to the devout.