This contemporary combo of a grey long sleeve t-shirt and jeans is very easy to pull together without a second thought, helping you look on-trend and ready for anything without spending too much time searching through your wardrobe. Round off with a pair of black leather casual boots to upgrade this look. In the winter months, when practicality is key, it can be easy to surrender to a less-than-stylish look in the name of convenience. This look, however, is a striking example that you can actually stay cozy and remain stylish at the same time during the winter months. If you often wonder how to dress as a guy in his twenties, this ensemble is a practical example.