The artist was the eldest daughter of John Carwardine of Thinghills Court, Withington, Herefordshire, and his wife Anne Bullock, a miniature painter. She also practised miniature painting, regarded as a genteel pastime for a woman. It seems that Penelope took up painting as a means of earning a living after her father ran into financial difficulties from around 1754. Cawardine exhibited at the Society of Artists in 1771 and 1772.

Cawardine painted many fashionable sitters including Lady Anne Egerton, the Earl of Coventry, Maria Gunning, Countess of Coventry (Wallace Collection) and Alice, the Countess of Egremont (Kenwood). James Boswell the diarist visited her home on March 15, 1763 to call on Lord Eglington who was having a miniature done, and described her in his London Journal as a ‘a very good-looking, agreeable woman’.

She moved in artistic circles and was painted by George Romney, John Downman and Thomas Bardwell. She is said to have been a friend of Sir Joshua Reynolds and his sister Frances, and apparently Reynolds painted a portrait of one of her sisters as a present for her. (The only record of this is in Algernon Graves and William Vine Cronin’s A History of the Works of Sir Joshua Reynolds P.R.A., 1899, where a brief entry for Miss Cawardine states ‘Sat in 1777’).

Her brother Rev. Thomas Carwardine (1734-1824), was rector and clerk of Earl's Colne Priory, Essex and a close friend of Romney, who was godfather to his daughter Anne (b.1779) and a frequent visitor to their house. Romney painted his portrait in 1772.

Penelope Cawardine married James Butler, organist of Ranelagh and St. Margaret's, and St. Anne's, Westminster in 1763 at St James’s, Piccadilly. After her marriage she worked much less, as the social customs of the day dictated.

The National Museum of Sweden owns the only other recorded drawing by Cawardine, drawn in a very similar style to the present work. It shares the characteristic diagonal hatching of the red chalk, is on similar laid paper and is cut into a rough oval in the same way.

Examples of her miniatures can be found in the Wallace Collection, the Victoria & Albert Museum, Kenwood House, the Museum of Fine Arts, Houston and the Tormey-Holder Collection.

Cyril Fry (1918 -2010) was a dealer in British drawings who owned a gallery in Jermyn Street. Fry and his wife Shirley amassed a substantial private collection over the course of his career.