White men have realized persistent advantages in high-status leadership positions in the workplace. Theories of gender inequality in leadership, including the “glass escalator” theory, consider only how this issue functions within occupational contexts and have yet to assess whether or how such patterns of inequality occur across institutions and may persist throughout the education-to-occupation pipeline. Using nationally representative data on U.S. high school students, the authors test for early evidence of racialized glass escalator effects by examining leadership disparities within the feminine-coded field of performing arts activities, which serve as an upstream approximation of feminized occupations. The authors find that although boys are less likely to participate in performing arts than girls, conditional on participating, they are significantly more likely to be leaders. White boys, in particular, have a strong leadership advantage compared with all other schoolmates, and especially to girls of color. The significant disadvantage girls of color face relative to White boys in attaining leadership within feminized domains in high school parallels established patterns in the occupational sphere. To the extent that early leadership experience begets future skills, opportunities, and pursuit of leadership positions, such early disadvantages may be expected to compound over the life course, influencing gendered and racialized role expectations and sorting.