In this chapter, through a focus group with members of Delta Sigma Theta Sorority, Inc., the authors query a set of highly politically engaged Black women about the importance of appearance to this group of political elites. As a historically Black Greek Letter Organization, this sorority has, throughout its history, upheld restrictive and controlling cultural norms that disproportionately impact Black women. Yet, the authors’ findings demonstrate that while there are different preferences and tactics that Black sorority-member voters think are most useful for other Black women to gain elected office, those voters are uniform in their desire to see successful Black women political elites. The authors also observe a generational split regarding the perceived political implications for Black women candidates with natural hair, which the focus group participants tie back to respectability politics. The chapter concludes by highlighting the differences in how younger Black sorority members think about the politics of appearance and the implications for these differences for the future of Black women political elites.