'In La Pia de’ Tolommei, Rossetti creates a character and scene from Dante’s Divine Comedy through the use of symbols. Here, La Pia sits upon the ramparts of the castle. The surrounding foliage alludes to her frustrating and miserable situation. The climbing fig tree framing her face symbolizes fruitfulness, and the sprigs of ivy on lower right corner represent clinging memory or fidelity in marriage. She plays with her wedding ring ("fair jewel") that symbolizes how a once joyous event now represents her unfortunate predicament. The sundial in the lower left corner is a reminder of the passing of time, or the coming of death, and the wheel of fortune motif on it refers to life changes. The rosary lying on an open prayer book refers to her name La Pia, which translates as "The Pious." Old love letters from her husband also symbolize the passing of time. The bundle of lances on the ground serves as a threatening barrier both compositionally and symbolically to the landscape below and her potential freedom. The red and pink banner of her husband draped across them reminds us of her captivity and that her once-beloved husband is now her jailer. Black crows flying above are thought to symbolize verse five of Rossetti’s poem "Sunset Wings" from 1871, about love that changes, never to be relived. The cloudy sky and gray barren landscape create a grim setting to this sad tale. La Pia’s contemplative expression is one of melancholy and introspection.

Rossetti often designed the frames to enhance the subject matter. On the frame for La Pia, he engraved the passage from the poem in both Italian and English in which La Pia’s spirit speaks to Dante:

The model for this painting is Jane Morris, wife of William Morris, a fellow artist and good friend of Rossetti. This is especially meaningful because Rossetti was in love with Jane Morris. He uses this passage from Purgatory to express his own unhappy romantic experiences with a woman who is married to, and in a sense, prisoner of a man she does not love.'[2]