This combo of a dress shirt and a black skater skirt embodies casual cool and casual style. If you wish to immediately smarten up your look with one single item, why not complete your ensemble with black leather ankle boots? In winter, when warmth is crucial, it can be easy to settle for a less-than-stylish outfit in the name of convenience. This outfit, however, is a good illustration that you can actually stay snug and remain seriously stylish in winter.