Make a dark green check wool blazer and black chinos your outfit choice for laid-back sophistication with an alpha male take. Put a different spin on your ensemble by rounding off with a pair of dark brown leather double monks. As you can see here, it's very easy to look seriously stylish and stay warm when cooler weather comes, all thanks to outfits like this one. So if you need outfit inspiration for dressing as you mature into your 30s, this ensemble is a good example.