Wellington was born in Gloucester and studied art there for three years, then in Birmingham and at the Slade. He was a close friend of Camden Town Group members Spencer Gore and Harold Gilman. Spencer Gore introduced him to Sickert, and he spent the summer of 1906 with Sickert near Dieppe. He lectured at the National Gallery (1919-1922), became Principal of the Edinburgh College of Art for ten years until 1942, and later returned to the Slade as a lecturer for two years until 1949. He wrote monographs of William Rothenstein and Jacob Epstein in the mid 1920s and showed his work at the New English Art Club, the Royal Academy and with the London Group. A one man show was held at Agnews in 1963. “To draw and to paint has been a pleasure and even a necessity” he remarked. His 1915 painting, The Big Barn, Frampton Mansell is in the collection of the Tate Gallery, London.

This self portrait was exhibited at the Allied Artists' Association in 1905.