If the situation calls for a polished yet killer getup, you can easily opt for a black and white double breasted blazer and chinos. And if you need to easily spruce up your look with one item, why not complement this look with black leather derby shoes? If you're already bored of your fall style options, this getup just might be the inspiration you are looking for. This pairing shows that looking stylish as a gent in his 50s is not that hard.