Title VII of the Civil Rights Act of 1964 (Title VII) prohibits discrimination against men because they are men and against women because they are women. This familiar characterization of the Act has been quoted in dozens of sex discrimination cases to support a narrow view of who is protected against sex discrimination in this country. When transsexuals file suit, “[e]mployment discrimination jurisprudence at both the federal and state levels ... captures transsexuals in a discourse of exclusion from social participation. This wide net, using a remarkably refined system of semantic manipulations, snags all claims launched by transsexuals and reveals that no matter how a transsexual frames her discrimination claim, it will fail.” In this Article, I explore whether those words, written after a thorough examination of employment discrimination claims brought by transsexuals in both federal and state courts, need revision in light of recent case law suggesting that the courts are prepared to recognize gender stereotyping as a viable legal theory of sex discrimination for both men and for women. In Part II, I describe the fictional case of a transgendered worker suing her employer for sex discrimination under Title VII of the Civil Rights Act of 1964 and the challenges faced by the law students working on both sides of the matter. In Part III, I explore the current contours of the gender stereotyping theory of sex discrimination and consider how useful such a theory could be to transgendered employees seeking redress for sex discrimination under Title VII of the Civil Rights Act of 1964. I conclude that sex discrimination claims brought by transgendered workers still confront enormous obstacles and that, despite the expanded judicial recognition of gender stereotyping claims, will continue to be difficult to advance into the future.

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