In this chapter, the author looks at the media-generated picture of gender within business and finance. Drawing on perspectives from visual culture studies and the concept of mediatization from communication studies, she argues that visual representations of leadership and power in the media do in fact matter. Accordingly, the author investigates portraits of the financial elite within the contemporary Norwegian press, with an emphasis on how the depiction of finance is gendered, and the consequences that such gendered images might have. Her principal interest is in visual portraits, and draws on perspectives from visual rhetoric and visual studies. She refers to other studies on similar topics, such as the gendering of politicians, but in part she contextualizes the visual representation of the financial elite with written portraits of the same group. The author pays attention to a new online community named 'Leaders in heels' that aimed to create female leaders and to 'nurture, inspire and empower women.