Whilst gender segregation in Saudi Arabia is a much researched topic, the existing literature usually focusses exclusively on women. It is hence little surprising that gender segregation tends to be regarded primarily as a limitation of women’s mobility and freedom of movement. The question of how gender segregation and other gender-related practices in Saudi Arabia affect the lives of men is hardly ever addressed. The proposed paper deals with the much debated topic of gender segregation in Saudi Arabia, considering both men’s and women’s perspectives. It traces changing concepts of gender segregation and relations in the city of Jeddah from around 1900 to the early twenty-first century through the history of shopping. Drawing on historic photographs, autobiographies and travel accounts, the paper will show that, until the mid-twentieth century, shopping in Jeddah was primarily done by men because women were ideally not to be seen in the streets. The numerous shopping centres that proliferated in the city form the 1980s on used to be gender-divided until recently, offering women of diverse social backgrounds spaces to socialise outside the home. Arguing that gender segregation constrains the movements of men and women alike, my paper challenges the widespread notion that men in Saudi Arabia benefit from the strict segregation regime while women suffer from it. The case of gender segregated shopping centres illustrates this point because, until recently, men’s access to them was as much regulated as women’s, if not more. Based on anthropological observations conducted between 2008 and 2019, I argue that shopping malls in Jeddah are indeed more than just places of commerce. They provide opportunities for men and women to meet and interact with each other. The paper also shows how those whose personal attitude deviates from the official gender policy deploy different strategies to circumvent it, thus re-negotiating the official politics of gender. Under the reign of crown prince Muhammad bin Salman, gender segregation was lifted in Saudi shopping malls and restaurants. Even in newly mixed public spaces, a constant awareness of gendered rules of conduct and mutual caution is required of both women and men, because the notion that visual contact should be avoided prevails.