"To define is to limit", Lord Henry states, and Mrs. Dalloway "would not say of anyone [...] that they were this or that". Why then are the respective novels mostly read - and in recent adaptations rewritten - in denial of their genuinely ambiguous designs? Bringing the two literary classics together for the first time, their shared concerns regarding textual and sexual identities are revealed. Challenging an established critical record commonly related to Oscar Wilde's and Virginia Woolf's own mythologised biographies, this study underscores the value of constantly rethinking labels by liberating the texts from the limiting grip of categorical readings.