Consider wearing a blue blazer and grey pants if you're aiming for a clean, fashionable outfit. If you need to easily rev up this getup with footwear, add dark brown suede chelsea boots to the equation. During the winter months, when comfort is the priority, it can be easy to settle for a less-than-stylish look in the name of practicality. But this look is a bright example that you totally can stay warm and remain equally stylish in the winter months. Definitely a never-failing option if we're talking fashion for middle-aged guys.