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My article, which begins by noting the fluke meeting between writer James Joyce and film star Marlene Dietrich in a Paris restaurant, considers the importance of masquerade and gender performativity in three texts of the late 1920s: an extract from Joyce’s final novel, Finnegans Wake, first published in 1925; Dietrich’s film, The Blue Angel (1930); and Joan Riviere’s psychoanalytic essay, ‘Womanliness as a masquerade’ (1929). After critically assessing the term ‘masquerade’ and Riviere’s reflections on it, I discuss the significance of Dietrich’s self-made costumes for The Blue Angel, arguing that she recognises the playful potential of the masquerade. Following this, I discuss the gender performativity of ALP, the heroine of Finnegans Wake, noting that her chapter of the novel shares with Dietrich’s and Riviere’s texts an emphasis on gender instability and shows how this can be performed through fashionable dress. I end by noting that Joyce, a male modernist often criticized for his reductive representations of women, is highly sensitive to the relationship between fashion and gender at this point in time.