Remo Ruffini, the trailblazing chairman and C.E.O. of Moncler, has never been much for convention, even when he was a twentysomething fashion entrepreneur selecting a starter home. Why settle into a serviceable apartment in, say, Milan when you can install yourself in a 19th-century masterpiece that looms over the shoreline of Lake Como? In 1987, after selling his first fashion brand⁠—a purveyor of preppy Americana called New England⁠—Ruffini purchased Villa Palatina, a relatively run-down compound located in the same city where he grew up.

While the compound comprises four residences, Ruffini and his wife, Francesca (the founder of F.R.S For Restless Sleepers), share them with the couple’s sons, Pietro, 30, and Romeo, 27. Around 10 years ago, Ruffini enlisted the Paris-based design firm Gilles & Boissier to weave the structures together and mastermind a full-scale renovation of the house and its gardens.