Vidutė Gumbytė (1949–2021), who was known as Rožytė (Rosie) by residents of the city, strolled the streets of Vilnius for almost five decades. Her story was unique, her style of fashion was eccentric, her lifestyle was idiosyncratic. In this article, I analyse Vidutė Gumbytė-Rožytė’s story as a Vilnius legend. I argue that Vilnius residents were fascinated by her freedom from social norms, her unusual sense of fashion, and the mystique that surrounded her persona. Her story is a story about the city of Vilnius, which became freer, wealthier, and more tolerant of otherness in post-Soviet times.