Infuse style into your day-to-day fashion mix with a black and white crew-neck t-shirt and charcoal skinny jeans. For something more on the classier end to finish this outfit, introduce casual boots to the equation. During the winter months, when functionality is a must, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a vivid example that you can actually stay comfy and remain stylish during the winter months. When it comes to casualwear for middle-aged gentlemen, this combination is ideal.