For relaxed dressing with a city style take, consider wearing a black and white plaid long sleeve shirt and white ripped jeans. And if you need to effortlessly perk up your look with one item, complement this look with white and blue canvas low top sneakers. When it comes to dressing for summer-to-fall weather, nothing beats a neat combo that transitions easily between seasons. Those who are curious how to pull off cool casual looks as you go through your 20s, you have your answer.