Consider wearing a grey shearling jacket and black jeans for a casual level of dress. For times when this look looks too classic, tone it down by slipping into a pair of grey canvas low top sneakers. In the winter months, when warmth is crucial, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. This ensemble, however, is a practical illustration that you can actually stay snug and remain stylish at the same time during the winter months. If you're not sure how to dress as a guy in his 20s, this combo is a practical example.