A grey long sleeve shirt and a white crew-neck t-shirt? This is easily a wearable getup that you could rock a version of on a day-to-day basis. For a more sophisticated spin, introduce black leather chelsea boots to the mix. In the winter season, when warmth is essential, it can be easy to settle for a less-than-stylish outfit. But this outfit is a bright example that you can actually stay comfortable and remain equally stylish during the winter season. Rest assured this combination is something you can totally wear as a 30-something Millennial guy.