We explored articulations of lesbian styles, fashions, and ways of dressing in mainstream fashion and media outlets within the United States during the twentieth and twenty-first centuries. Based upon our findings, we propose that there was trending ambivalence and multiple assemblages across space and time where the mainstream media did not necessarily perpetuate a single stereotypical or essentialist way of conceptualizing fashionable lesbians or lesbian fashions. However, we also noted across time a divide between representations of celebrity lesbians and the contemporary lived experience of ordinary lesbians. Though the press acknowledged this divide on occasion, they also established, circulated, and reinforced this difference. According to the press, while lesbians have been 'chic' since the 1990s-whether they embraced a butch or femme esthetic-the best way to be lesbian was to be rich, white, and fashionably dressed.