Over the past few decades, the Italian clothier Brunello Cucinelli has created a highly profitable, globally present, luxury fashion line while reading medieval monastics. Entrepreneurs and business ethicists might be intrigued to explore how this apparent paradox is resolved in Cucinelli’s manner of running his company—a practice inspired, in part, by drawing widely from works in the Western humanistic and religious canon. From his study of St. Benedict and St. Francis, among others, Cucinelli has found ways of squaring particularly daunting circles: the correlation between luxury and quality; the meaning of labor for human dignity in an age of excessive production and consumption; the role of philanthropy in tandem with profit-making; and the transfiguration of the corporate CEO into an abstemious and caring abbot. By reading from Cucinelli’s chosen philosophical touchstones, and exploring the effects of that reading on his day-to-day operations, we may glean insight into his particular understanding of luxury as it relates to his “humanistic enterprise” in the world of business, and to the specific demands such an undertaking makes on those who would be its leaders and stewards. The extent to which Cucinelli’s business ethics might be translated beyond his Italian context, and in entrepreneurial initiatives other than high-end fashion, is also considered