For relaxed dressing with an urban finish, reach for a white and navy gingham long sleeve shirt and black ripped skinny jeans. Spice up this outfit by rounding off with a pair of white leather low top sneakers. Dressing warmly is the key to surviving cold temps, but this ensemble is a practical illustration that you can do it with style. Gentlemen who are curious how to dress fashionably as you make your way through your 20s, you have your answer.