During the past few years, the fashion market has undergone continuous and far-reaching processes of change and renewal. The unexpected mixing between and the hybridization dynamics of fast fashion, sportswear, and luxury fashion have given rise to the birth of a new product market category that successfully recombines their elements and characteristics: luxury streetwear. Off-White, which was only created in 2013 but already chosen as the most popular brand in the world by 2019, undoubtedly—more than any other brand—led this revolutionary trend inside the fashion industry. Owing to its unique ability to selectively draw on youth culture and creatively merge it with elements that have traditionally been associated with luxury fashion (e.g., the garments’ prestige, quality, and class-distinctiveness), Off-White was able to access the conservative and hyper-competitive luxury arena even as it questioned and restyled the market’s canons and paradigms. However, Off-White’s success cannot solely be attributed to the disruptive ideas of a visionary artist, founder Virgil Abloh, nor to the mere creation of products perceived as unique. The rise and success of Off-White happened within the framework of a systematic implementation of a competitive strategy that is substantiated in an eclectic use of the marketing mix variables and the development of virtuous collaborations with other established brands. It is a strategy that, given Off-White’s astonishing financial performances and brand-related results, cannot be considered anything less than a success. But what are the ingredients of this recipe for success? How did Off-White climb the luxury fashion Olympus with streetwear clothes? What does the future hold for fashion and, more specifically, for the streetwear category?