Ammi Phillips had a prolific and lengthy artistic career, painting hundreds of portraits across the Northeastern United States for more than half a century. One aspect of Phillip’s enduring success was his ability to adapt and reflect the aesthetic of each era during which he worked. From early advertisements published in 1809 and 1810, we know that Phillips was already painting in Massachusetts, and that he promised to portray subjects in the prevailing fashion of the day. This beautiful portrait marks a transitional work between the dreamy and luminous visions of 1812–1819 and the increasing realism and deepening palette of the 1820s, while still exhibiting elements seen in portraits of earlier periods. ⁠ ⁠ Ammi Phillips (1788–1865), Young Man and Red Drapery, Connecticut, Massachusetts, or New York, United States c. 1820, Oil on linen, 29 1/2 × 23 1/2". Collection American Folk Art Museum. Gift of Louise W. Floeckher in memory of Louis M. Colton, 2010.5.1. Photo by Gavin Ashworth.