Daedalus was an inventor and slave of Minos King of Crete who had previously helped the king trap his adversary, Minotaur, in a labyrinth. Here Daedalus is depicted in a servile posture fitting feathers on his youthful and handsome son, Icarus. Icarus flew too close to the sun, causing the wax attached to the feathers to melt and drowned in the sea. Leighton was a very successful painter of the Victorian era. He subscribed to the aesthetic movement and completed projects on classical and Renaissance classism. His paintings sought to satisfy the nostalgic desire by the British aristocracy to reminisce about the Golden Age of Greco-Roman cultures. The art is consistent with his other works along the same theme of mythography depicting iconic characters in Greek legends.

Leighton depicts the pair preparing for the flight against a background of objects that symbolize the Greco-Roman culture. They stand on a high precipice where the wind is strong. Daedalus intricately ties the wings around his son's body. The sky is intensely bright, while the ground below is hazy with mist, just like in the Ovid legend. Behind them stands a statue of Athena sitting on a Doric column. Leighton was also inspired by the mythographic works of Van Dyck on the same subject. In Van Dyck's painting, the two figures resemble the father and son, just like in Leighton's work.

Both Leighton and Van Dyck used the legend to sharply contrast the differences between the young and aged male nudes. The two painters also captured the contrasting attitudes of the pair with the father showing concern and trepidation where the son showed excitement and anticipation. Other sources of inspiration include a Roman cameo featuring a physically imposing Icarus being fitted with wings on a podium. The cameo was part of the book Daedalus: or the Causes and Principles of the Excellence of Greek Sculpture (1860) authored by Edward Faulkner.

Icarus and Daedalus follow the theme of appropriating the Greco-Roman culture that is evident in Greek Girls Picking up Pebbles by the Sea. Other common characteristics of his paintings include the use of contrasting colors. In both works, he uses both bright and dull draping for clothing. The juxtaposition of light and dark colors is also evident in The Fisherman and Syren. Leighton had a penchant for using the sculptural style in his paintings characterized by smooth surfaces and marble sharp images that is evident in the Greek depictions. The painting is part of The Farringdon Collection available for viewing at Buscot Park, Oxfordshire.