Such must-haves as a white and red and navy plaid dress shirt and navy skinny jeans are the perfect way to introduce some cool into your casual styling repertoire. You can get a little creative with shoes and tone down your ensemble by rounding off with tan snow boots. During the winter months, when warmth is imperative, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is hard proof that you can actually stay comfortable and remain seriously chic during the winter months.