Swing into something polished yet on-trend in an olive wool waistcoat and white chinos. For maximum style, introduce a pair of brown suede derby shoes to this getup. In the winter season, when practicality is everything, it can be easy to settle for a less-than-stylish getup in the name of practicality. But this getup is a good illustration that you totally can stay warm and remain stylish at the same time in the winter season. This pairing is something older gentlemen can wear with confidence.