Reach for a charcoal blazer and grey wool dress pants if you're aiming for a sleek, stylish outfit. Rounding off with a pair of brown leather casual boots is an effective way to introduce a sense of stylish nonchalance to this look. This one is a viable idea if you're putting together a cool outfit for in-between weather. This combo proves that figuring out how to dress well as a middle-aged man is totally doable.