This chapter examines the underwear market in the context of fashion and cultural branding. The discourses on idealization and body positivity, as well as luxury and functional underwear corresponding to them, were considered. The Russian underwear market was analyzed. Based on the studied data, a qualitative stage of the study was compiled, consisting of interviews of consumers and experts. It was revealed that consumers’ expectations partially do not coincide with the offer of Russian brands of “luxury underwear.” It was also revealed that women wear “luxury underwear” not only on “special occasions” to demonstrate femininity, but also in everyday life “for themselves.”