This publication explores the rich intersections of portraiture and fashion in the art of the English painter Thomas Gainsborough (1727–1788), one of the most sought-after society portraitists of his age and a continued inspiration today. Gainsborough, whose importance was akin to that of later society artist John Singer Sargent, made hundreds of portraits, becoming one of the leaders of the fledging British School of artists. Very much a part of the social dynamic of the time, portraiture is described as a “means by which artists and their subjects could reinforce, resist, or break rules of social order.” The engrossing text examines how fashion was understood, often in complex ways, in Gainsborough’s time; how the artist would sometimes revisit a portrait to update a style; and how the documentation of both sitter and garment can be deciphered centuries after the creation of a work. Entries are provided on each of the twenty-five works in the exhibition that the catalogue accompanies. The book explores how and why Gainsborough and his sitters chose the trappings in which they would be immortalized in paint. From dukes and duchesses to the once-enslaved Ignatius Sancho, Gainsborough captured the essence of his contemporaries. A century after Gainsborough’s death, his portraits experienced renewed popularity among wealthy American collectors such as the Fricks, Vanderbilts, and Huntingtons, who coveted his works for their private collections. This book provides a comprehensive understanding of Gainsborough’s oeuvre and his time, and is an invaluable resource for understanding the longstanding appeal of eighteenth-century art.