Hughes was the nephew of the Pre-Raphaelite painter, Arthur Hughes, under whom he first studied. He then entered the Royal Academy Schools and worked with Holman Hunt, helping to complete some of his later works (including the St. Paul’s version of The Light of the World). He was also in touch with Burne-Jones and knew George Macdonald, to whose daughter he was engaged before she died. He worked mainly in watercolour, painting literary themes of a symbolist nature and portraits; he also specialised in red chalk portrait studies, for which he was much admired.
The model here is the same as for Hughes’s Fra Lippo Lippi of 1893 and Oh, what's that in the Hollow...? of 1895. Victoria Osborne (in her MPhil thesis on Hughes at Birmingham University, 2009) discussed Hughes's red chalk drawings in some detail and noted, 'In a review of the winter exhibition at the RWS in 1893, the critic of The Athenaeum drew attention to a red chalk drawing by Edward Robert Hughes, [Fra Lippo Lippi], praising it as “in several respects, the finest work here”. [The picture] was classed by the reviewer with a group of drawings by Edward Burne-Jones [with whom Hughes had correspondence about which kind of chalk was the most authentic] and studies of heads by Frederic Shields as one of “a series of fine examples of drawing proper in monochrome, which will delight painters and critics trained in the higher technique.” … Hughes’s drawing is a virtuoso display of chalk technique in which the young man’s features are sensitively modelled in softly-graded areas of tone and the effect of light shining through the semi-transparent fabric of his hood is deftly captured’.