Singer Sargent created the portrait following commissioning by Catherine Lasell Whitin of Whitinsville. Catherine greatly admired Ada Rehan, a famous theatrical actress during that period and had commissioned Singer to create a portrait of the artist during a dinner party in December 1893. While Sargent had predicted to paint the piece in March, he did not begin painting it until April. Apparently, Ada Rehan, the subject of the portrait had been taken ill, which was occasioned by the demands of the heavy theatrical season.

The portrait shows Miss Rehan wearing an off-shoulder gown made of ivory satin with the sleeves made of silk gauze. She is holding a white feather fan that belonged to Mrs Graham Robertson who was sitting next to Sargent. Though the sitting happened during the early summer months, the portrait experienced notable background problems. Singer wanted to use a Persian rug as the backdrop, but it overwhelmed the portrait such that it appeared as the principal art. John Singer Sargent decided to show traces of the pattern under the existing surface. Additionally, neither Miss Rehan, Sargent nor Mrs Whitin were pleased with the original background. Thus, a seventeenth-century tapestry was used instead.

The artist created the Ada Rehan portrait during the realism movement. The style was devoted to reflecting what the painter saw without idealising the truth. This portrait reveals the personality and the individuality of the subject and Singer employs an unusual composition and lighting to create a striking effect. It is this feature that made Ada Rehan's portrait stand out from other such artists (Bonnat, Madrazo and Chartan) at the Corcoran Gallery of Art during a loan exhibition in 1898. When the portrait was first showcased, the art amateur noted the great contrast the Ada Rehan portrait had from others. He explained that it shone with increased brilliance and displayed great quality of skill.

Many masters and styles inspired Sargent, but his main inspiration for this piece was from Velazquez. Velazquez was a great Spanish master and is remembered as the first artist to do away with under-drawing and under-painting and choosing to apply paint on the canvas directly. Singer travelled to Spain to learn about his works under the supervision of Carolus-Duran, a painting teacher who used Velazquez's methods.