So as you can see, it doesn't take that much effort for a man to look casually classic. Just team a navy blazer with blue jeans and you'll look awesome. Up the classiness of your look a bit by rocking a pair of dark green leather brogue boots. We recommend this one if you're searching for a snug look that's as stylish as it is comfortable. This getup proves that as a middle-aged gentleman, you still have a wide array of styling options.