Against a backdrop of legislative change that sees the taking of private sexual images underneath the clothing of a non-consenting other being made a criminal offence - upskirting - there is a need to understand the public's judgments of and motivations to perpetrate said behavior. In this study (N = 490), we investigated whether judgments of upskirting differed as a function of the sex of the person who was upskirted (male, female) and their perceived attractiveness (attractive, unattractive), as well as how variation in voyeuristic interest, belief in a just world, and dark personality traits predicted judgments of and proclivity to engage in upskirting. We consistently observed more lenient judgments of upskirting behavior when the person who was upskirted was attractive and male, with such judgements predicted by older age across all conditions. Moreover, proclivity to engage in upskirting was predicted by past voyeuristic behaviors, higher psychopathic personality, and being male and of older age. We discuss our findings in the context of needing to qualitatively understand the rationale underpinning these judgments, combating barriers to disclose victimization, and practitioner implications.