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Following on from my investigation of the pious and social efficacy of prolific family portraiture within the Tornabuoni chapel of S. Maria Novella, this paper finds a similar mix of motives informing the portrayal of contemporary faces in the guise of religious characters. These include devotion or allegiance but incentives for such masquerades further range from humility to audacity, penitence to celebration, homage to ridicule. Several previously unrecognized examples of portraits in disguise painted by Domenico Ghirlandaio are the starting point here for a study of their connection to art theory and devout customs of the time as well as their social and visual impact in a religious context. Particular attention will be given to the depiction of patricians, merchants and scholars as lowly characters like beggars or shepherds, and to reasons why they have been overlooked, which have implications for our modern assumptions about the parameters of portraiture.