Fashionable and comfortable, this off-duty pairing of a navy denim jacket and dark brown chinos offers variety. Finishing with casual boots is a guaranteed way to add a bit of classiness to this ensemble. In the winter months, when warmth is critical, it can be easy to settle for a less-than-stylish getup in the name of convenience. But this getup is a shining example that you totally can stay snug and remain equally stylish in the winter months. And if we're talking outfit ideas for gents in their fifties, this combination is perfect.