This pairing of a brown houndstooth overcoat and charcoal dress pants comes in handy when you need to look seriously sharp. A pair of brown leather derby shoes is a surefire footwear style here that's also full of character. When it's one of those gloomy fall days, sometimes only a neat look like this one can brighten things up. Interested in dressing ideas for maturing gentlemen? This ensemble goes straight to your inspiration folder.