For a cool and relaxed getup, try teaming a navy windbreaker with khaki chinos — these two items fit nicely together. For times when this look appears all-too-classic, tone it down with dark green athletic shoes. When leaves turn yellow and red and fall takes over, you'll appreciate how ideal this ensemble is for summer-to-fall weather. Ideal if you're scouting for some amazingly inspiring style for middle-aged men.