You’d be hard-pressed to think of a brand that embodies Italian sprezzatura more than Italia Independent. Founded in 2007 by entrepreneur Andrea Tessitore and Fiat heir/perennial best-dressed-list denizen Lapo Elkann, Italia Independent designs clothing, eyewear, shoes and accessories that play to the modern playboy’s penchant for looking effortlessly chic. The label’s offerings range from light blue cotton blazers and gray down jackets to crisp oxford button-down shirts perfect for the boardroom. Italia Independent also designs a line of women’s sunglasses, including velvet and silver-studded wayfarers as well as classic, no-frills aviators.