If you gravitate towards casual style, why not take this pairing of a black vest and black skinny jeans for a walk? Go off the beaten path and shake up your look by slipping into black suede ankle boots. In the colder months, when warmth is the priority, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. But this ensemble proves that you can actually stay comfortable and remain equally chic in the colder months.