Winterhalter was born in the Black Forest where he was encouraged to draw at school. In 1818 he went to Freiburg to study under Karl Ludwig Schüler and then moved to Munich in 1823, where he attended the Academy and studied under Josef Stieler, a fashionable portrait painter. Winterhalter was first brought to the attention of Queen Victoria by the Queen of the Belgians and subsequently painted numerous portraits at the English court from 1842 till his death.

Prince Leopold (1853–84) is pictured wearing a dress (often worn by young boys at this time). He was the fourth and youngest son of Queen Victoria and Prince Albert. A scholarly child, he attended Christ Church in Oxford. He was a haemophiliac, suffered from epilepsy and died at the age of 31.

Signed and dated: Fr Winterhalter / 1855. Inscribed on the back with the names of the artist and sitter and the date, June 1855.