Rosenberg was often unable to afford models and his oeuvre includes many self portraits. The earliest ones are delicate in the melancholic Romantic tradition. Between 1912 and 1915, however, under the influence of the Slade, Rosenberg began to shed this persona in a series of leaner, bolder self portraits which display his transition to modernism. This is Rosenberg’s final self portrait; it is also his final finished work as a painter. Drawn in the trenches on crumpled, poor quality brown paper, possibly salvaged from a parcel, its fragile state documents this important part of its history. The portrait relates closely to a sketch from a letter, entitled 'Self Portrait Sketch in Tin Helmet' (c.1916, Imperial War Museum) of which Rosenberg joked to his family that it was ‘The New Fashion boiler hat – the trench hat’.