This thoughtful and sophisticated book views Gertrude Stein's life and writings through the lens of transgender theory. Reframing earlier scholarship that falsely assumes that Stein's masculinity was a misogynist manifestation of self-hatred, Chris Coffman argues that her gender was transmasculine and affirms her masculinity as a vital force in her life and work.

This book uses Stein's writings - and others' literary and visual texts about her - to illuminate the ways her transmasculinity was formed through her relationship with her feminine partner, Alice B. Toklas, and through her masculine homosocial bonds with modernist figures such as Jane Heap, Pablo Picasso, Ernest Hemingway and Carl Van Vechten.