Go for a simple yet laid-back and cool option by pairing a navy windbreaker and tan shorts. When in doubt as to what to wear on the footwear front, complete your getup with a pair of white canvas low top sneakers. This combination is a tested option if you're looking for a great, season-appropriate combination. Gentlemen wondering how to pull off cool off-duty style as you are making it through your teens, you have your answer.