Any watch enthusiast worth his salt would know this slogan by heart: “A Patek Phillippe watch will never really be yours. You merely look after it for the next generation.” Legacy, dynasty, and heritage. The three make an alluring case for an enduring heirloom watch that teaches responsibility to your lineages. A luxury timepiece is, after all, meant to be cherished, and well-cared for, as it travels between hands of different generations. Ahead, we picked five modern heirloom watches for the millennial man, with a mix of updated classics and recently launched award winners.