For an outfit that's truly GQ-worthy, dress in a waistcoat and khaki dress pants. Want to dial it down in the footwear department? Add a pair of dark brown brogues to your look for the day. During the winter season, when warmth is top priority, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is a clear example that you totally can stay toasty and remain equally stylish during the winter season. Wondering how you should dress as you slip into your 50s? This ensemble is an amazing example.