Major Sir William Orpen (1878-1931) was an Irish artist who worked mainly in London as a popular and commercially successful portrait painter.
The present portrait was commissioned by the sitter's parents, Sir Harold and Lady Stiles, to mark their daughter Dorothy's 21st birthday. Orpen was a family friend and stayed with them when painting the portrait. The painting demonstrates Orpen's vigorous and painterly style. Dorothy grew up in the Scots medical world. A companion portrait by Orpen indicates that she was a keen golfer at a time when, following the example of Margot Asquith, it became fashionable for young women to practice the sport. There were a number of important courses near the Stiles’ family home at Whatton Lodge, Gullane in East Lothian. She was one of Gullane Ladies Golf Club's most prominent members. She was Honorary Secretary in 1913 aged 18, Captain in 1929-30 and again in 1947-48. She was made Honorary Member in 1972. Dolly's status at the club can be judged from her being the only person to have been Captain twice and that the companion portrait was used for the cover of the GLGC centenary history.