This thesis explores the complicated representations of women in Playboy magazine and its related media, re-evaluating these portrayals through the lenses of the gaze, objectification, and agency. Spanning the magazine’s inception in 1953, to its post-Hefner digital transformation, this study investigates how Playboy has both reflected and shaped cultural constructions of femininity over time. By employing an interdisciplinary and multi-method approach, including feminist critical discourse analysis, visual methodologies, semi-structured interviews with Playboy staff, and auto-ethnographic practice-based research centred on self-portraiture, this work delves into the complexities of Playboy’s depictions of feminine sexuality. Focusing on the contributions of women who have produced, consumed, and posed for Playboy, the thesis shifts attention away from Hugh Hefner’s to foreground the women involved in shaping the brand. Drawing on Ann Cahill’s concept of derivatization (2010) and Susanna Paasonen et al.'s work on objectification (2021), the thesis introduces the concept of complicated empowerment to frame the interplay between agency, objectification, and commodification within Playboy’s patriarchal “Entertainment for Men” framework. This analysis reveals how women working within or represented by Playboy navigate, perform, and at times subvert its constructed ideals of desirable hyper-femininity, challenging simplistic binaries of empowerment and sexual objectification. By situating Playboy within evolving feminist discourses this thesis demonstrates how Playboy’s portrayals of women negotiate cultural tensions surrounding femininity, empowerment, and sexualisation. It further interrogates the brand’s contemporary alignment with feminist ideals amid movements such as #MeToo, exploring how these shifts complicate its legacy while reshaping narratives of feminine sexualities from within. This study contributes to feminist media scholarship by offering a nuanced, historically situated analysis of Playboy as a site of both constraint and possibility.
