Team a navy and green plaid long sleeve shirt with navy skinny jeans if you seek to look casually dapper without trying too hard. And if you need to instantly step up this ensemble with one single item, throw in a pair of burgundy leather casual boots. In the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish look. This look, however, is a practical illustration that you can actually stay cozy and remain equally stylish in the winter months.