Make a waistcoat and black check chinos your outfit choice if you're going for a proper, on-trend getup. Want to go all out on the shoe front? Add a pair of loafers to the mix. In the colder months, when comfort is a must, it can be easy to surrender to a less-than-stylish look in the name of functionality. This look, however, is a bright example that you totally can stay cozy and remain stylish during the colder months. A combo to make any 20-something gentleman look more respectable and mature.