When the setting allows off-duty dressing, wear a white crew-neck t-shirt with black chinos. Play down the formality of your look by rocking a pair of black and white athletic shoes. In winter, when warmth is a must, it can be easy to settle for a less-than-stylish outfit. But this outfit proves that you totally can stay warm and remain stylish at the same time during winter. Overall, a perfect demonstration of laid-back fashion for over-30 gents.