Born in Dumbarton in 1859, Strang attended the Dumbarton Academy before entering the Slade at the age of seventeen where he studied under Alphonse Legros, who was to have a lasting influence on Strang's art. Although he continued to paint, he focused on etching and printmaking dominated his oeuvre until the turn of the century. During the latter part of his life Strang etched less and painted more, producing a series of portrait drawings inspired by Holbein's drawings at Windsor of sitters such as Sir Lawrence Alma-Tadema (1908); the young Edward, Prince of Wales (1909); and Thomas Hardy (1910). As a portrait painter Strang experimented with many styles, and his most famous paintings include his bold portrait of Vita Sackville West, Lady with a Red Hat (1918, Kelvingrove Art Gallery & Museum, Glasgow) and the highly original Bank Holiday (1912, Tate, London).

In an Art Journal article about Strang, Frank Newbolt declared that 'In his painting there are two obvious qualities which attract attention besides the effort to eliminated the unnecessary and ineffective. The first is the simplicity of colour; and the second, the almost indescribably effect of fine composition' (Art Journal, 1910, p. 49). This effect is clearly seen in this striking self-portrait. Strang produced a series of self-portraits over the course of his career. A comparable, slightly smaller example, also painted in 1917, where the artist is wearing the same suit and tie is in the National Portrait Gallery, London. The pre-occupation with the First World War is evident in both portraits. Other examples can be found in the National Galleries of Scotland and in the Tate, London.