A tan wool turtleneck and charcoal wool chinos make for the perfect foundation for a casually cool outfit. White leather low top sneakers are a surefire way to bring a sense of stylish effortlessness to this outfit. When it comes to dressing for transitional weather, nothing beats a cool combination that can take you from season to season. Gents who wonder how to rock classic and casual outfits as you cruise through your 20s, you have your answer.