This pairing of a white crew-neck t-shirt and grey check chinos delivers comfort and confidence and helps keep it simple yet current. When it comes to shoes, complement this ensemble with a pair of black suede low top sneakers. So as you can see, it's very easy to look seriously stylish and stay snug when chillier weather comes, thanks to this look. Wondering how to nail casual dressing as you pass the big 4-0? This combo is the perfect answer.