Wear a sweatshirt with skinny jeans for a neat and fashionable outfit. For something more on the dressier end to complete your ensemble, complement your getup with black leather casual boots. During the winter months, when functionality is imperative, it can be easy to settle for a less-than-stylish getup. This getup, however, is a shining example that you can actually stay cozy and remain equally stylish during the winter months. Those who are curious how to dress stylishly and look good as you work your way through your 20s, you have your answer.