This combo of a light blue denim jacket and a crew-neck t-shirt is proof that a simple off-duty look can still look seriously stylish. Add an elegant twist to your outfit by finishing off with a pair of dark brown leather desert boots. During the winter season, when comfort is a must, it can be easy to settle for a less-than-stylish getup in the name of practicality. However, this getup is a good illustration that you can actually stay comfy and remain stylish at the same time in the winter season. As you go into your 30s, you want to start dressing more like a mature gentleman. In this case, getups like this are ideal as inspo.