Men’s apparel is often thought of as staid and restrained, especially when compared to women’s fashions. Yet Old Master and Modern portraits tell a different story, presenting centuries of male sitters who have taken great care with what they wear and how they wear it. Until the late eighteenth century, men flaunted their style and social position with costumes fashioned from lavish textiles, often surpassing the opulence of their female counterparts. Later, though men generally adopted more sober suiting, exquisite tailoring and sophisticated accessories became hallmarks of a new and refined brand of expensive elegance. Today, the attire of the fashion-conscious man challenges and redefines traditional concepts and emblems of masculinity. The portraits presented here celebrate menswear, an inexhaustible source of beauty and innovation.