Modernism has long been understood as a radical repudiation of the past. Reading against the narrative of modernism-as-break, Pragmatic Modernism traces an alternative strain of modernist thought that grows out of pragmatist philosophy and is characterized by its commitment to gradualism, continuity, and recontextualization. It rediscovers a distinctive response to the social, intellectual, and artistic transformations of modernity in the work of Henry James, Marcel Proust, Gertrude Stein, Oliver Wendell Holmes, John Dewey, and William James. These thinkers share an institutionally-grounded approach to change which emphasizes habits, continuities, and daily life over spectacular events, heroic opposition, and radical rupture. They developed an active, dialectical attitude that was critical of complacency while refusing to romanticize moments of shock or conflict. Through its analysis of pragmatist keywords, including "habit," "institution," "prediction," and "bigness," Pragmatic Modernism offers new readings of works by James, Proust, Stein, and Andre Breton, among others. It shows, for instance, how Stein's characteristic literary innovation—her repetitions—aesthetically materialize the problem of habit; and how institutions—businesses, museums, newspapers, the law, and even the state itself—help to construct the subtlest of personal observations and private gestures in James's novels. This study reconstructs an overlooked strain of modernism. In so doing, it helps to re-imagine the stark choice between political quietism and total revolution that has been handed down as modernism's legacy.