This refined combo of a grey plaid waistcoat and grey dress pants is a common choice among the sartorially superior chaps. To bring a dose of stylish effortlessness to this outfit, add a pair of black leather brogues to the mix. As the weather turns cooler, you'll find that an ensemble like this is ideal for the season. Just because you're in your 50s, doesn't mean you can't look trendy, and this pairing demonstrates exactly that.