In this article, I deal with the disparagement of femininity and trans persons in multiple levels of our culture, including in some feminist theory and Shakespearean criticism. I point out that contemporary culture, patriarchal institutions, and some feminist positions share misogynistic stances towards expressions and embodiments of femininity; and these perspectives carry over into some criticism, as well as our academic institutions and classrooms. I examine the double-standard that is often applied to feminine-gendered behavior and bodies in contemporary culture and the profession. In so doing, I address the points of tension and common ground between feminist, queer, and transgender theories in the field of Shakespeare and early modern studies. In addition, I advocate and suggest ways to implement transfeminist approaches to teaching Shakespeare within the contexts of popular culture and contemporary media.