A tank and a charcoal herringbone overcoat are a nice pairing that will easily take you throughout the day and into the night. You know how to elevate this getup: black tassel loafers. During the colder months, when warmth is crucial, it can be easy to settle for a less-than-stylish outfit. But this outfit is a practical illustration that you totally can stay comfortable and remain equally stylish during the colder months. Men who are curious how to wear cool off-duty outfits as you make it through your 20s, this outfit should answer your question.