We love how this combo of a waistcoat and grey plaid dress pants instantly makes any man look refined and stylish. When this getup is too much, dial it down with black and white oxford shoes. During the winter season, when warmth is paramount, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. But this ensemble is a good illustration that you can actually stay warm and remain stylish during the winter season. This getup proves mature gentlemen can very well slay in the style department.