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The landscape of college campuses in the United States continues to grow more diverse. With this diversification comes a need for those interacting with students to continue to enhance their level of multicultural competence. Bell hooks’ Teaching to Transgress: Education as the Practice of Freedom has long been regarded as a seminal text on creating a more multiculturally competent classroom environment. In this chapter, I examine the potential for applying the concepts from Teaching to Transgress—which I call “transgressive teaching”—to the work of student affairs professionals; particularly, those who influence the dominant group identities of White, heterosexual, and male, while examining the ways in which transgressive teaching challenges them to approach their work in new ways. These challenges can also serve as insights into ways in which transgressive teaching can disrupt influences of White privilege, heterosexism, and patriarchal dominance on the work of student affairs professionals who benefit from these systems of power. The chapter concludes with recommendations for future research and application to the practice of student affairs professionals in higher education.

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