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Gendered organization theorists have long argued that “jobs” are not gender-neutral, but rather are constructed by and for male bodies, male heterosexual sexuality and men’s emotions. As such, symbolic expressions of womanhood in the workplace may stigmatize and marginalize women workers, necessitating complex management of their professional image to align with masculine worker norms. Yet not all women workers have the same extent of control over their professional images to engage in this aesthetic labor. Women in uniform, particularly in male-dominated occupations, are often formally required to dress like men. To investigate how women in male-dominated uniformed professions manage their professional image at work, I draw on data with 40 U.S. soldiers who served during a period of expanded grooming and appearance regulations. By comparing men and women’s responses to new feminized uniform options, I identify a “ponytail paradox” for women in uniform. On the one hand, because the new options for individual gendered expression were afforded only to women, adopting them underscored women’s dissimilarity and marginalization, requiring more aesthetic labor to conceal appearances that invited sexist reactions. In addition to concealing their femininity, some women maintained their appearance as usual, appealing to a traditional masculine-typed aesthetic they had grown to accept. On the other hand, new opportunities for gendered expression made some women participants feel more like themselves at work despite the gendered harassment that ponytails and earrings incited. Further, organizational characteristics such as place, rank and leadership status condition the degree of agency women soldiers have to “deal” with their womanhood in the first place. Findings reveal the complex relationship between professional appearance standards and equity in male-dominated organizational contexts.