This chapter offers a sweeping examination of the shifting nature of selected book covers by Iranian writers in English over the last several decades. It highlights how politics, reader and market interests have historically affected book covers. It begins by examining how certain historical perspectives constructed a stereotypical vision which led to a recurring series of covers on books by Iranian and other Middle Eastern writers: namely, that of half-veiled faces of women. Then, pivoting on the controversial 2009 Iranian presidential elections, it highlights how social media introduced a new kind of image about the Middle East leading to changes in book covers. When people on social media began presenting new images of Iran where men and women fight alongside on the streets, women’s visible public presence began to challenge the illusive Western belief of Iranian/Muslim women as passive and private. Iranian women’s public presence, viewed globally, shifted how Iran was seen. Iran was no longer a strictly gender dichotomous society as imagined. Consequently, the lens gazing into Iran became less focused on close up encounters of veiled women. There was now an interest in more overall, current and sweeping narratives of men and women that contextualized contemporary Iranian life. With this new interest, came a new wave of book covers. Almost gone were the half-veiled faces of women, as the new narratives reflected the larger mystery that Western readers were trying to decipher: the Iranian nation as a whole. Consequently, covers began to shift from close ups to overall depiction of the Iranian nation and cities. In some, mysterious cityscapes replaced women’s faces. This paper, traces the socio-political history which led to the shifting nature of book covers by Iranian writers in English from that of half-veiled women to one replaced by the city as a site of desire.