If you're on a mission for an off-duty but also seriously stylish look, pair a black bomber jacket with skinny jeans. You can get a little creative with shoes and elevate your getup by rocking a pair of black leather chelsea boots. When you have one of those bleak autumn days, sometimes only a neat outfit like this one can get you out the door in the morning. This pairing demonstrates that looking stylish as an older gentleman is not that daunting a task.