The aim of this chapter is twofold. We will first discuss current research as well as key theoretical and methodological paradigms to investigate linguistic landscapes and illustrate, how space is conceptualized within a variety of different research contexts and objectives. We will then move on to illustrate the pragmatics of linguistic landscaping by drawing from a case study that investigates the Philippine jeepney as a mobile communicative space that exhibits and constructs a variety of competing discourses embedded within Filipino culture, among them colonialism, nationalism, migration, Christianity, social conservatism, and patriarchy. To conceptualize the jeepney as a mobile space we will draw from Kress and van Leeuwen’s (2006) grammar of visual design and Scollon and Scollon’s (2003) notion of geosemiotics. In bringing together text, visual design and wider social context, the jeepney becomes an assemblage of material object, (colonial) history, discourse, and affect. It emerges as a site where visual representations of language are indicative of wider political, social and economic processes and further highlights, how those processes and relations are both reaffirmed and challenged