If you like comfort dressing, why not pair an oversized sweater with a skater skirt? Want to go all out when it comes to shoes? Complete your outfit with black leather ankle boots. In the winter season, when warmth is paramount, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. However, this ensemble is a stark illustration that you can actually stay snug and remain totaly stylish in the winter season.