Marrying a grey waistcoat with navy wool dress pants is an on-point pick for a sharp and classy look. You can take a more relaxed approach with footwear and introduce a pair of dark brown leather derby shoes to the equation. During the colder months, when functionality is the priority, it can be easy to surrender to a less-than-stylish getup. This getup, however, proves that you can actually stay comfy and remain equally stylish in the colder months.