If you want to look stylish and stay comfy, pair an oversized sweater with a skater skirt. If you want to immediately perk up your getup with shoes, why not add a pair of black leather ankle boots to the equation? During the colder months, when warmth is crucial, it can be easy to surrender to a less-than-stylish getup in the name of practicality. But this getup is a shining example that you can actually stay warm and remain equally totaly stylish in the colder months.