Augustus John painted this portrait of his second partner, Dorothy (Dorelia) McNeill (1881 -1969) for the annual Exhibition of Fair Women organised by the International Society at New Gallery, London in February-March 1909 where it was bought by Dr C. Bakker. It was purchased from him in 1910 by the Contemporary Art Society in their foundation year. Therefore it was their first purchase and the first work by the artist to enter Tate's collection when it was presented by the CAS, along with 26 other artworks, in 1917.
Reviewers compared John's Woman Smiling picture to works by Van Dyck and Manet and until then he had been better known as a draughtsman but Roger Fry, a co-founder and co-editor of The Burlington Magazine, as well as co-founder of the CAS the following year, wrote: ‘Here at last Mr John has “arrived” in painting as definitely as he has long ago done in his drawings.’ Fry also called it a ‘gypsy Gioconda‘, referring to Leonardo’s Mona Lisa (1503/06). Dorelia had designed her own dress with high waist and long skirt setting a fashion for bohemian costume.