Loving the way this pairing of a grey plaid waistcoat and grey dress pants instantly makes any gentleman look stylish and sophisticated. Go ahead and complete your look with a pair of black chunky leather oxford shoes for a more relaxed twist. When it's one of those bleak autumn days, sometimes only a neat ensemble like this one can get you to face the outside world. An ensemble like this will make any man in his fifties look better than any of his peers.