Kathryn MaddenJun 26, 2026 – 5.00amFor fashion designer Tommy Hilfiger, who built a billion-dollar empire on preppy all-American glamour, sailing has always been a fashionable pursuit. “Some of my earliest memories are of enjoying boat races as a kid,” he says. “Watching from the shoreline, the energy felt thrilling and magnetic. The open water stood out to me as a place of freedom and unlimited possibility. This is something I wanted to bring into the brand from day one.”Hilfiger is not alone. In the 1940s, Coco Chanel purchased Mathilde, a steel-hulled yacht with five staterooms, to assert her independence in a man’s world. Giorgio Armani’s superyacht, Main, was a lavish floating home, meticulously designed by the late fashion luminary.Subscribe to gift this articleGift 5 articles to anyone you choose each month when you subscribe.Subscribe nowAlready a subscriber? Fetching latest articles