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This paper presents a critical ethnography of an example of fashion's mediating cultural work: sneakers and North American gay men. This rich example presents fashion with a specific garment and wearers, yet mediating work in multiple directions, exemplifying fashion's ambivalence and flexibility. I will describe three positions taken, articulated around gender, and their relations to dominant culture: (1) sneakers are feminine and rejected in opposition to dominant culture; (2) sneakers are masculine and embraced in assimilation into dominant culture; and (3) sneakers are masculine and embraced in opposition to dominant culture. Beginning from a position of ambivalence (like fashion itself), I will elaborate historical and cultural contexts, showing a particular garment, among a particular group, put to varied ends. However, multiplicity is not necessarily progressive. While there are counter-hegemonic aspects to these sneaker positions- resisting stereotypes, embracing difference, denaturalizing sex, gender, and sexuality constructions- other aspects preserve the status quo. While admiring the creativity evidenced, I ultimately question positions untaken, such as embracing femininity.