This outfit with a dress shirt and blue ripped skinny jeans isn't super hard to score and is open to more creative experimentation. Why not take a more casual approach with footwear and throw in snow boots? In the winter season, when practicality is a must, it can be easy to surrender to a less-than-stylish look in the name of practicality. This look, however, is a shining example that you totally can stay cozy and remain equally stylish in the winter season.