This off-duty combo of a navy windbreaker and tobacco chinos will catch attention for all the right reasons. For something more on the casually cool side to round off this outfit, introduce high top sneakers to this look. When you're having one of those dull fall days, sometimes only a kick-ass look like this one can get you out the door in the morning. Off-duty combinations for stylish older men aren't actually that hard, as you can see.