Fashion constitutes an essential part of the modern world, where clothes perform many functions: signifying the place of individual bodies in social, economic, and sexual orders, as well as being a commodity. In the early 20th century, with the advent of literary modernism, clothes became a favoured metonym for modernity. Prompted by the late 19th century women’s dress reform, women started to dress themselves in various garments: some to acquiesce the tradition and convention, others to resist them. Particularly, the lesbian women often adopted male garments or oriental clothes to express their sexual preferences. Avant-garde artists introduced new styles of fashion. Virginia Woolf and her Bloomsbury friends were among the cultural rebels. They threw fancy dress parties where they wore costumes to flout the established. The Omega Workshops offered unconventional clothes for women. Women’s clothes served as a sketchbook in which to express many different things such as ideas, gender preferences, or belief systems. Woolf’s novel Orlando provides a rich text to read out these various aspects of clothes, social and individual, both in cultural and historical contexts. Woolf seems to use clothes as a metaphor for writing. As Orlando changes from a man to a woman, her clothes change accordingly and sometimes deliberately. By choosing clothes, Woolf seems to suggest, one’s sexual identity can be changed. Adopting clothes of both sexes, Orlando transcends the sexual barrier of her body and mind, and eventually succeeds in acquiring the androgynous mind, which Woolf esteems as an ideal state of the mind for a writer. This paper will re-read Orlando in terms of clothes to explore the parallelism between clothes and writing and the dynamism between gender and writing intricately woven in the text.