To achieve an off-duty menswear style with an edgy spin, pair a navy crew-neck t-shirt with grey sweatpants. Want to play it up in the shoe department? Complement your ensemble with white and navy leather low top sneakers. During the winter season, when warmth is key, it can be easy to settle for a less-than-stylish outfit. However, this outfit is hard proof that you can actually stay warm and remain equally stylish in the winter season. This combination demonstrates how to dress well and look good as you drift through your 20s.