This essay primarily looks at the relationship between gender and art through history,

by comparing the two main characters of Virginia Woolf's Orlando (1928) and Ali

Smith's How to Be Both (2014), and their shared qualities of being gender-bending,

century-travelling artists. The theoretical background to this comparison is Angeliki

Spiropoulou's (2010) theory on the shared opinion of Walter Benjamin and Virginia

Woolf, on how art history is a constructed narrative, which, as Woolf has illustrated by

her use of Orlando in Orlando, has favoured male artists over women artists and their

work. My analysis of Woolf’s Orlando, and the subsequent analysis of the artist

Fransescho del Cossa's role in How to Be Both shows that Smith's similar use of

century-travelling and gender-bending in her character reinforces Woolf's point that

artistry has been unfairly gendered throughout history, and that this has slowly changed

towards a larger acceptance of women artists. Furthermore, How to Be Both especially

highlights the importance of understanding historical accounts as constructed

narratives, by making the reader question who the narrator behind Fransescho's story

is.

Each novel also shows the importance which clothes have in marking a person's

gender, and therefore the characters are directly affected in their artistry depending on

the clothes they wear. Moreover, this essay shows that both novels have a similar

perspective on the creativity process, with both of their characters detaching themselves

from their own gender identity when creating art through painting and writing.