If you enjoy a more relaxed approach to fashion, why not pair a crew-neck t-shirt with light blue ripped jeans? White and black high top sneakers will pull the whole thing together. During winter, when practicality is above all, it can be easy to settle for a less-than-stylish outfit in the name of functionality. However, this outfit proves that you totally can stay snug and remain equally stylish in winter. Gents wondering how to dress fashionably as you make your way through your 20s, you have your answer.