This off-duty combo of a navy windbreaker and white chinos is a winning option when you need to look cool but have no extra time. If you're on the fence about how to round off, complete this look with white and black canvas low top sneakers. This one is a wonderful pick when it comes to a kick-ass summer-to-fall outfit. This outfit should prompt anyone who wasn't sure about sporting casual outfits as a 40-year-old.