A dark brown blazer and navy wool dress pants are absolute essentials if you're planning a classy closet that matches up to the highest sartorial standards. Add dark brown leather loafers to the equation and the whole look will come together wonderfully. Dressing smartly is the key to surviving subzero temperatures, but this outfit is a practical illustration that you can do it with style. This combination demonstrates that looking stylish at 40 plus is totally doable.