For a look that's classy and totally wow-worthy, team a grey waistcoat with grey dress pants. Tone down the dressiness of your outfit by rocking brown fringe leather loafers. When you have one of those dull fall days, sometimes only a kick-ass outfit like this one can get you out the door in the morning. This combination shows that looking stylish as you age into your 40s is not that daunting a task.