This laid-back combo of a grey print hoodie and black jeans is simple, on-trend and extremely easy to imitate. Balance out your ensemble with a dressier kind of shoes, such as this pair of black leather chelsea boots. With an ensemble like this in your winter closet, you'll manage to stay snug and look stylish despite the extreme weather. Gentlemen who wonder how to wear cool off-duty style as you move through your 20s, you have your answer.