The closet of any discerning gent should always include such wardrobe heroes as a blazer and charcoal wool dress pants. On the shoe front, this getup pairs well with dark brown derby shoes. In the winter season, when warmth is essential, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. But this ensemble is a stark illustration that you totally can stay toasty and remain equally stylish during the winter season. This combination proves older gents can still very well turn heads.