James Madison, by Charles Willson Peale Philadelphia artist Charles Willson Peale painted this miniature portrait of Madison in 1783, paired with one of Madison’s fiancée, Kitty Floyd, the sixteen-year-old daughter of a New York congressman. Meant to be worn like jewelry (note the pin on the right), miniatures were tokens of mutual affection. After Floyd broke off the engagement, Madison waited eleven more years before finding a wife.

Library of Congress, 3g04097.