This relaxed pairing of a shirt jacket and grey shorts can go different ways depending on the way you style it out. Consider burgundy boat shoes as the glue that will bring your getup together. So if it's a warm summertime day and you want to look dapper without putting too much effort, this ensemble will do the job in next to no time. Those who are curious how to dress fashionably as you progress through your 20s, you have your answer.