Teaming a light blue chambray dress shirt and grey wool dress pants will create a confident, rugged silhouette. Want to dial it down in the footwear department? Complete this outfit with burgundy leather derby shoes for the day. In winter, when warmth is essential, it can be easy to settle for a less-than-stylish getup. However, this getup is a striking example that you totally can stay snug and remain equally stylish during winter.