From literature, the flâneur is a French term which defines a male figure, an active observer of modern city life in Europe, whose main pastime is strolling around the city. Originating in the 19th century, the term personifies the urban explorer devoid of a purpose. This idea became more appreciated during modernity’s height as cities were urbanized and industrialized. The flâneur became a source of romantic inspiration where artists and writers majored in imagining the contemporary sophisticated aloof figure of the city. French poet, Charles Baudelaire is popularly known as the pioneer of the term after writing about it in his essays during the modern life in Paris, later to be termed ‘The Arcades Project’. The writings describing the flâneur, which have been completed by Walter Benjamin, focus on the conditions of alienation and freedom offered by the metropolitan city and thus, leaning toward modernism. In modern works of imagery and writing, the silhouette of a flâneur interests those who want to depict the idea of city life and delve into concerns of facelessness, watching, and self-reflection. This spirit of strolling or pondering in a contemporary city is invoked through the use of photography, performance, and installation by artists like Sophie Calle and Janet Cardiff who have transformed the flâneur archetype. As such, the figure of a flâneur continues to offer great possibilities for investigating the relationship between the space of the city and the life of its people.