Men experience discrimination every day at work and at school because they fail to look or behave like real men. Most courts now hold that men can prove sex discrimination by presenting evidence that the defendant harassed or bullied the plaintiff because he fails to conform to sex stereotypes. But judges in these cases are reluctant to find that defendants intended to discriminate “because of sex,” which is required to state a valid claim under statutory anti-discrimination law. Instead, judges routinely grant defendants’ motions for summary judgment and to dismiss based on little more than their own ideas about what masculinity means and whether the plaintiff’s gender presentation matches those ideals.

This Article encourages judges to analyze sex stereotyping evidence contextually, taking into consideration factors such as the parties’ geographic and spatial locations, race, and class. If a plaintiff’s gender presentation differs from the dominant gender norms in the relevant context, that difference, accompanied by harassment, should support an inference of discriminatory intent. A contextual intent approach recognizes that what it means to be gender conforming is different depending on who and where one is, and that sex stereotyping evidence likewise varies case-by-case. Attention to context will lead to more accurate determinations of whether a plaintiff’s gender differs from what is accepted and expected, and thus whether it is fair to infer that a plaintiff was harassed for those differences.

This Article challenges implicit social and legal assumptions that real masculinity exists. By deconstructing manhood’s meanings, it seeks to create more space for all men and women to perform gender freely. If the law better protects men who deviate from rigid gender constraints, the law also sends a normative message that masculinity and femininity—whatever those terms mean to each individual—are equally valuable. If men feel safe to behave in less conventionally masculine ways, perhaps femininity will gradually cease to be a tool that divides real men from failed men, and perhaps masculinity will lose its privileged status in the gender hierarchy.