This combo of a grey crew-neck t-shirt and grey skinny jeans is extra stylish and creates instant appeal. For something more on the elegant end to complete this getup, add a pair of dark brown leather casual boots to the mix. During the winter season, when functionality is a must, it can be easy to surrender to a less-than-stylish getup in the name of functionality. This getup, however, is a practical illustration that you totally can stay warm and remain stylish at the same time during the winter season. Those who are curious how to dress well in your mid-20s, you have your answer.