Such items as a grey crew-neck sweater and navy skinny jeans are an easy way to infuse extra cool into your casual fashion mix. You can follow a more classic route on the shoe front by rocking black leather mid-calf boots. In winter, when warmth is essential, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. But this ensemble is a shining example that you can actually stay toasty and remain equally stylish during winter.