If you’re a jeans-and-a-tee kind of guy, you'll like the simple combo of a black hoodie and black skinny jeans. Our favorite of an endless number of ways to round off this outfit is a pair of casual boots. In the winter months, when warmth is key, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. This ensemble, however, is a good illustration that you totally can stay comfy and remain stylish during the winter months. As a 30-something man, you want to start dressing like an adult man. If that's the case, ensembles like this are perfect as inspiration.