Why not dress in a puffer jacket and an olive gingham skater skirt? These two items are super comfy and look stunning paired together. Feeling venturesome today? Elevate your ensemble by finishing off with dark brown knee high boots. In the winter season, when practicality is critical, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a stark illustration that you can actually stay comfy and remain equally seriously chic in the winter season.