In the thirty years that have passed since the publication of Alan Bray's landmark book Homosexuality in Renaissance England, feminist and queer scholars have asked and answered the question - how queer was the transvestite theatre, in a variety of ways. This chapter describes some salient trends that have shaped critical interpretations of three transvestite comedies: William Shakespeare's Twelfth Night, John Lyly's Galatea, and Thomas Middleton and Thomas Dekker's The Roaring Girl. It provides the diverse ways conjunctions of transvestism and homoeroticism obtain both on the early modern stage and in early modern culture. The chapter uses the term "queer" to signify an array of social and sexual practices, arrangements, and peoples that, when put into discourse, confront or undermine the (perceived) dominant culture's views on gender and sexuality. It deployes "queer" to designate those conjunctions of crossdressing and same-sex desire that in the process of challenging dominant beliefs and attitudes, imagine alternative arrangements and practices.