If you're scouting for a casual street style yet sharp look, choose a hoodie and light blue jeans. Inject your outfit with a touch of sophistication by finishing off with tan suede casual boots. In the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish getup. However, this getup is a practical illustration that you totally can stay toasty and remain equally stylish in the winter months. Gents who are curious how to dress stylishly and look good as you move through your 20s, you have your answer.