If you gravitate towards off-duty looks, why not consider teaming a grey crew-neck sweater with navy jeans? And if you need to immediately play down your getup with one piece, add a pair of black canvas high top sneakers to the equation. When temps are dropping and autumn is in full swing, you'll love this getup as your uniform for unpredictable fall weather. Off-duty combos for stylish middle-aged guys aren't actually that hard, as you see here.