If you enjoy comfort dressing, consider teaming a grey crew-neck sweater with black skinny jeans. For a more sophisticated take, complement this look with a pair of black suede ankle boots. In the colder months, when functionality is imperative, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is hard proof that you can actually stay comfy and remain incredibly chic during the colder months.