For a casually cool look, wear a white and blue long sleeve shirt and light blue ripped jeans — these two items fit perfectly well together. Let your sartorial chops truly shine by rounding off your outfit with a pair of high top sneakers. In the winter months, when practicality is everything, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look proves that you can actually stay cozy and remain equally stylish in the winter months. Those who wonder how to wear modern casual dressing as you make it through your 20s, this combination should answer your question.