A long sleeve shirt and black ripped skinny jeans are a street style pairing that every modern gent should have in his casual sartorial collection. Kick up the classiness of your look a bit by finishing off with a pair of low top sneakers. In the winter season, when comfort is essential, it can be easy to surrender to a less-than-stylish look. However, this look is a clear example that you can actually stay toasty and remain equally stylish during the winter season. Those who wonder how to look stylish as you drift through your 20s, you have your answer.