Within this figurative portrait we find the saint looking directly into the sky, seemingly in need of guidance. He is dressed in modest clothing and holds only some scrawls of paper in his hands. He appears old in this portrait, with a white beard and bald head. He wears no shoes, and just a simple grey robe. Behind him is a rocky landscape which does not push too far into the distance, with golden paint then used to decorate the rest of the background further behind. One can still make out shapes in that part of the composition which suggests that perhaps more detail existed in the work previously but that some of the paint has worn away in the centuries that have passed since. That said, all of the detail closest to us is well preserved, with several items on the ground around Saint Jerome, including a small animal. Two trees are placed on either side of the painting which helps to frame the work, where vertical objects capture the main content in the centre of the painting.

Fra Angelico would have been in his mid twenties if the date of this piece is accurate, and at this stage he was working in a less ambitious manner and he continued to work on his artistic technique and style, whilst also starting to attract new patrons for the first time. It would only be later that finance and fame allowed him to take on complex projects in which assistants could provide a supporting role. Whilst his talents with portraiture are always present here, there is none of the rolling hills found in his later landscapes, nor the complex arrangements of figures right across a canvas that we might see later on. Saint Jerome was famous for translating the Bible into Latin, and this is perhaps depicted in this scene with some symbolic touches, but his life also included a number of other important achievements too.

The Penitent Saint Jerome has at times been attributed to the likes of Masolino, Masaccio and Giovanni Toscani, all fellow Florentines, but the new attribution to Fra Angelico has been accepted by most as the likely source. This painting features a small coat of arms in the bottom left which has led to some speculation around the purpose of this painting, with it perhaps being gifted as a wedding present though this has never been confirmed. The Princeton Art Museum also features some other interesting artworks such as Rainy Day, Fifth Avenue by Childe Hassam, Landscape: Shinnecock, Long Island by William Merritt Chase, George Washington at the Battle of Princeton by Charles Willson Peale and also Anthony van Dyck's The Mocking of Christ.