This laid-back pairing of a black hoodie and skinny jeans is a foolproof option when you need to look great in a flash. Feeling bold today? Class up your look by rounding off with tan suede chelsea boots. With an outfit like this in your winter arsenal, you're guaranteed to keep warm and look stylish despite the cold weather. Those who are curious how to sport modern off-duty looks as you drift through your 20s, this pairing should answer your question.