A windbreaker and charcoal wool chinos are stylish menswear items, without which our closets would be incomplete. Get a bit experimental when it comes to footwear and class up your look with casual boots. During the winter months, when warmth is top priority, it can be easy to surrender to a less-than-stylish look. This look, however, proves that you totally can stay comfortable and remain stylish at the same time during the winter months. Guys who are curious how to pull off classic and casual outfits as you make it through your 20s, this outfit should answer your question.