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Both race and gender are conceptualized as categorical in most scholarship about punishment inequality, often focusing on Black/White and male/female differences in punishment. Importantly, these categorical inequalities are frequently discussed absent their existence in racialized and gendered dynamic social systems, rendering categories as static variables. We consider how both race and gender interact in a dynamic process to shape punishment outcomes by focusing on colorism and masculinity. While colorism and masculinity might have consequences in many areas, we focus on pretrial detention. Pretrial detention is subject to substantial discretion by court actors, allowing for the introduction of racial and gendered bias in punishment. Drawing from a sample of adults arrested for felonies in Miami-Dade county (N=6888), we find that colorism is more directly consequential for men, but masculinity is consequential for women in terms of greater likelihood of punishment. For men, colorism is a greater stratifying mechanism than categorical (Black/White) groups. For women, colorism informs perceptions of masculinity. This contributes to literature on racial and gender inequality and punishment by finding that there are more continuous (and dynamic) differences for punishment outcomes based on skin tone and perceived masculinity, particularly in a context that is highly influenced by pigmentocracy.