 Penny was educated at Shrewsbury School and St Catharine's College, Cambridge, before undertaking his postgraduate studies at the Courtauld Institute of Art in London.His academic career began with a research fellowship at Clare Hall, Cambridge, after which he went on to teach art history at Manchester University.While still in his early thirties, Penny was appointed to the Slade Professorship at Oxford University and to a senior research fellowship at King's College, Cambridge.