Team a white dress shirt with charcoal dress pants if you're going for a proper, stylish ensemble. Black leather double monks will instantly play down a classic ensemble. During the colder months, when warmth is key, it can be easy to surrender to a less-than-stylish getup. But this getup is hard proof that you totally can stay snug and remain stylish at the same time during the colder months. A no-brainer pairing appropriate for gentlemen in their fifties.