Despite the earl's relatively well-documented public career, he remains something of a shadowy figure in terms of his personality. Oxford perhaps has more sources than most late medieval noblemen, though in quality or quantity they do not match those of his cousin, John Howard, but no full personal study could be written – the best that can be done in terms of appraising his character is to survey what we know of his activities outside of the political sphere, which allows a glimpse of a more rounded individual. Some of the evidence for such activities does, however, come from the earl's last testament, which must be treated with caution, as preparations for the afterlife are not necessarily the best guide to an individual's outlook on life being lived. Other sources, such as household expense accounts, provide detail on his day to day life, but were written by his officials, rather than the earl himself. In light of the lacunae in the evidence, much of what follows must be suggestive rather than conclusive.

Family relationships

It is clear that Oxford had a strong sense of his lineage, and that his relationships with members of his family mattered a great deal. One immediate reason why his family was so important to him may have been that he had lost so many members of it during his lifetime. In 1485, when forty-three, he had neither surviving grandparents nor parents, and three of his four brothers were dead.