Upon Further research I have found some more context for the painting of St. Augustine. St. Augistine was well known for his idea of the Catholic church as a "City of God", separate from the earthly cities. The castle on the left side of the picture that is hit by light and the slightly angled viewpoint give this suggestion that this castle on the hill is a high view of the church. In addition, this was likely painted for a Chapel dedicated to the Confraternity of Perugia, Il Perugino's home town. So the glorification of the confraternity's works through the representation of their good works through their traditional hoods and robes was likely intentional.
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