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Castagno showed an almost obsessive interest in naturalism in his portraits; the Portrait of a Gentleman in the National Gallery, Washington can today be safely attributed to him. The young man, portrayed in three-quarter profile and not in full profile as was the custom, is a typical Castagno figure, with his unmistakable strong sculpturalism.
This picture is one of the landmarks of Italian portraiture: the earliest surviving painted portrait in three-quarter view, with the figure, splendidly dressed in the most costly red, seen against the sky, shown to the waist, with his right hand clutching the long end of a hood worn over the shoulder.
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