This essay has been adapted from conference comments delivered at the “Remembering Langston Hughes: His Art, Life and Legacy Fifty Years Later” conference held at Princeton University, November 10–11, 2017. It ties together a number of prominent themes of Hughes's legacy. Through an analysis of the tension between the categories of identity that Hughes adopted and those he eschewed, it offers a commentary on longstanding academic debates concerning Hughes's perceived irreligiosity and sexual orientation. Based on lessons gleaned from Hughes's experimentalism and bold tradition of self-fashioning, it argues for a more expansive interpretation of these aspects of his life and work. While many scholars have interpreted Hughes as an atheist or antireligious, a more nuanced view of his life and the treatment of religion in his oeuvre reveals profound reflections on matters of faith. Similarly, it challenges straightforward interpretations of Hughes's personal life and sexual identity. Ultimately, the essay argues that Hughes’ art and his own embodied practice offer a model for approaching existential questions such as those of spiritual belief or sexual expression with more nuance and capaciousness.