Marry a grey turtleneck with black ripped jeans if you wish to look casually stylish without making too much effort. Amp up the dressiness of this outfit a bit by rounding off with a pair of casual boots. In the winter season, when practicality is paramount, it can be easy to settle for a less-than-stylish ensemble in the name of convenience. This ensemble, however, is hard proof that you totally can stay warm and remain stylish at the same time during the winter season.