To don a casual ensemble with a city style spin, try teaming a navy long sleeve t-shirt with blue ripped jeans. Hesitant about how to round off your look? Round off with dark brown leather casual boots to smarten it up. When you have one of those bleak fall days, sometimes only a cool getup like this one can get you out the door in the morning. Those who wonder how to pull off cool casual style as you head into your 30s, this pairing should answer your question.