John Barry made this miniature portrait of a woman, probably in the early nineteenth century, with watercolor on ivory. These small portraits were popular keepsakes at a time when painted likenesses were still largely the preserve of the wealthy. The sitter’s soft features, elaborate hairstyle, and ruffled dress, indicate a middle-class background. But to fully understand a piece like this we have to ask about the broader social conditions of artistic production. Was Barry self-consciously conservative or progressive? Did he accept or critique the institutions of art? Unfortunately, very little is known about his career or professional training. To find out more, we might consult period directories of artists, or search databases of auction sales, private collections, and museum holdings. What we discover would shape our understanding of the artistic, social, and institutional context that gave this intimate portrait its meaning.