Putting together a white and brown vertical striped dress shirt and a multi colored houndstooth overcoat will be a true testimony to your sartorial expertise. Go ahead and introduce brown leather tassel loafers to your outfit for an air of polish. As you can see, this combo is a really wonderful idea, especially for in-between weather, when the temperatures are dipping. This getup shows that as a guy over 40, you have a wide range of outfit options.