Abstract From the nation's first non‐white President, to prevalent narratives of demographic change, a surging reactionary Right and emerging social awareness of white identity, the social context in which white Americans relate to whiteness and white privilege has changed since the early 1990s foundations of whiteness studies. In this article we review work on white Americans and whiteness generally to grapple with their (dis)positions within, and provide a roadmap for sense‐making through, recent cultural and racial‐political developments. We begin with an overview of now canonical critical‐theoretical scholarship, set in the context of other (more limited) empirical work about specific white American subgroups. We highlight how these related, frequently overlapping, though certainly non‐synonymous tracks of inquiry into whiteness and white Americans have since evolved, emphasizing that iterative exchange between them may best situate potentially different, cross‐cutting orientations toward whiteness and privilege held by various contemporary American whites. We then focus our discussion on several socio‐historical developments that will have significant, if somewhat uncertain implications for the reproduction, possible transformation, and study of white America in coming years. Specifically, we detail literatures surrounding recent questions upon the shapes of the white color line, contemporary white nationalisms, and prospects for white antiracism.