Between 1828-1830, American illustrator Edward Williams Clay depicted fashionable Black men in satirical prints which suggested that free Black men in Philadelphia were social climbers dressing above their station. At the same time, the character of the Black dandy entered the American sartorial lexicon through stock characters in minstrel shows: Jim Crow, My Long-Tail Blue, and Zip Coon. The characters of these Black dandies in both print and performance marked fashionable Black men as perpetually fashionable and permanently lower class. It also suspiciously linked fashionability with Blackness. Can men’s fashion history help historians better understand the origins of the minstrel show?