Abstract This co-authored article draws upon two distinct genres of photography, police mugshots and amateur soldier snapshots, to illustrate the value of queer visual culture methodologies for how to think about the visualization of violence, masculinity and desire. Building upon two vastly different depictions of male to female cross-dressing, one produced between 1934 and 1938 by the Berlin police and Gestapo of a transvestite and the other produced between 1940 and 1944 by cross-dressing Wehrmacht soldiers behind the lines, we argue that in searching for evidence of intact identities, we overlook important ambiguities. We first show how different photographic traditions have framed gender and sexual non-conformity in the historical record and then go deeper into an image analysis. Drawing upon cross-dressing as a polyvalent performance of masculinity, as play, camp and an identity category, we explore how photographic sources help us better appreciate the multiple and sometimes coexisting layers of feminized masculinity at work during the Third Reich. By queering Nazi history and reading the police mugshots and amateur Wehrmacht photographs within and beyond their visual frames, we point out the limits of reducing every image of cross-dressing to an expression of an inchoate gay or trans identity and argue for analysis that embraces the multiple layers of histories gathered around visual sources.