Fascination with the life and times of William Shakespeare abounded in the Victorian world, especially in London, where American artist Edwin Austin Abbey settled permanently in 1883. The Bard's writings provided lifelong inspiration for Abbey: as a teenage writer, he used a pen name from Hamlet; from the age of 20 he illustrated hundreds of Shakespearean subjects for magazines; and in the 1890s he painted seven large Shakespearean scenes, including this canvas, which he exhibited at London's Royal Academy.

The theme of this painting is drawn from Shakespeare's Two Gentlemen of Verona. The title "Who is Sylvia? What Is She, That All the Swains Commend Her?" is the opening question in a song composed by Proteus, one of the many suitors (or swains) of Sylvia, the Duke of Milan's stunning daughter. All heads turn toward the regal beauty as she lifts the skirts of her Italian Renaissance-style gown while descending a brilliantly carpeted staircase. Each admirer gazes at her and reaches to play an instrument or to offer her a love token. The figure at far left presents a luxurious feather fan; the next man a small dog; and the figure leaning against the column bows in devotion, holding his hat in one hand and a book of poetry in the other.

The painting's shallow, frieze like composition is characteristic of Abbey's work during this period. Just as the space is constricted, so are several different events from Shakespeare's play conflated into a single moment. The canvas's compressed form and content, as well as Abbey's attention to period costume, have their roots in the English Pre-Raphaelite movement with which the artist was associated. His approach also evokes the pictorialist fashion in late Victorian theater, which valued elaborate visual spectacle over plot to the degree that Shakespeare's texts were often radically shortened to accommodate time-consuming changes of intricate costume and scenery.

Remarkably, Abbey did not begin painting in oil until age 40, when he was mentored by his close friend and fellow expatriate John Singer Sargent. He still labored over his ambitious canvases, however, and during or after the display of "Who Is Sylvia?" at the Royal Academy, Abbey scraped out Sylvia's head and repainted it from another model. He also changed her arms, which were crossed, to their present position holding her dress, which originally had a train at the right. Abbey selected the painting's intricate frame, featuring decorative bands of different motifs that echo the gleaming gold fabric details in the scene. This opulent object—with its gilded frame and richly colored canvas—must have appealed greatly to the wealthy American mining baron William A. Clark, who purchased it directly from the artist.