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This essay investigates the cultural and technological logics underpinning the design and operations of virtual fitting rooms. Virtual fitting rooms are full body–scanning technologies that look and function much the same as airport security scanners but, unlike their security counterparts, have been widely embraced by consumers. Virtual fitting rooms represent the latest technology in the fashion retail environment; at the same time, they are fundamentally connected to the expansion of surveillance culture in the United States. Analyzing the scientific discourse and methods that engineers and researchers employ to establish “the perfect fit” or the optimal “relation between the individual body and the particular garment,” this essay argues that the scientization of style both establishes and obscures the racial ideologies underlying judgments about fashionability. From hoodies to burqas to sagging jeans and “hoochie” dresses, the “bad fit” has historically marked racialized others as “misfits” who warrant heightened scrutiny, suspicion, surveillance, and discipline. Virtual fitting rooms rationalize and systemize these long-held cultural notions under the cover of technological color blindness.