A raincoat and black chinos are the ideal way to introduce muted dapperness into your day-to-day casual rotation. A pair of grey athletic shoes easily revs up the style factor of your look. Can you see how super easy it is to look seriously stylish and stay snug when chillier weather arrives, all thanks to ensembles like this? This combination should clear any doubts you had about wearing casual clothes as a man in his fifties.