A navy denim jacket and dark brown chinos have become must-have wardrobe pieces for most gents. Why not take a classic approach with footwear and complement your ensemble with a pair of black leather casual boots? You can see here that just because the temperature dipped to near-freezing doesn't mean your ensembles can't be both warm and seriously stylish. On the hunt for dressing ideas for middle-aged gentlemen? This outfit definitely goes to your inspiration folder.