Long-standing wisdom and academic research consistently agree that consumers choose attractive products and avoid ugly ones. And yet, multiple luxury brands successfully sell distinctively ugly products. This research provides an explanation, identifying distinctive ugliness as a signal of luxury and examining its impact on consumer choice. We explore this in seven studies, including a field study, a market pricing analysis, and five controlled laboratory experiments, three with consequential behavioral measures, incorporating a variety of fashion products, brands, aesthetic manipulations, and audiences. When products are from a non-luxury brand, consumers choose the attractive option and avoid the ugly. However, when from a luxury brand, consumers choose distinctively ugly products as often as attractive ones, not despite their ugliness but due to their ugliness and resulting ability to signal luxury. As such, brand prominence offers a boundary condition, as both a loud logo and distinctive ugliness serve to signal. Implications for both luxury and non-luxury brands are discussed.