This chapter examines how recent criticism highlighting genre, gender, and technology can inform our understanding of New Woman writing. Read from a “trans” perspective—across gender, genre, and technology—the New Woman emerges as a complex representative of how identity boundaries cannot be fixed. I situate reading from a trans perspective within existing criticism, including criticism that highlights New Women as literary innovators; journalists—writers who engaged Victorian views about race, empire, and various forms of disciplinary knowledge—and participants in aestheticism and decadence. I propose a new direction for New Woman criticism to supplement existing approaches, and I apply a trans approach to key texts by Sydney Grundy, Henrik Ibsen, Mathilde Blind, Constance Naden, “Victoria Cross,” “George Egerton,” and “Sarah Grand” to show how New Women writers created realms in which non-normative gender roles might be represented.