A navy sweatshirt and jeans make for the ultimate laid-back style for any man. And if you want to easily dial up your look with shoes, add dark brown leather brogue boots to this look. In the winter season, when warmth is prized, it can be easy to settle for a less-than-stylish ensemble in the name of functionality. But this ensemble is a good illustration that you totally can stay comfy and remain stylish at the same time in the winter season. This combo shows that in your thirties you have a wide array of dressing options.