This article examines the habits of looking that mediate perception in the self-consciously multiracial Southeast Asian island city-state of Singapore. I propose looking as a concept for understanding how perceivers work to transform ambiguous, ambivalent encounters with difference into determinate, visibly self-evident encounters with race. I argue that, in Singapore, habits of looking get materialized via a visual epistemology of race: as efforts to know others by knowing their race through multimodal assemblages of signs, with vision located at the apex of hierarchies of perceptual modalities. I examine informal interactions, state-produced media, and online commentary to show how language, race, and perception get co-naturalized (Rosa and Flores, 2017) in an asymmetrically power-laden image economy (Halliday, 2018; Poole, 1997). I show how looking enables perceivers to see through the eyes of authoritative others and track how hierarchies among perceivers get continually reproduced and revalorized despite continual failures on their own terms.