For an ensemble that's worthy of a modern sartorial-savvy guy and casually classic, consider pairing a brown overcoat with navy jeans. Go ahead and add dark brown leather derby shoes to this getup for an element of sophistication. When it comes to dressing for weird fall weather, nothing beats a cool combination that will keep you warm and looking your best. An outfit like this will help any guy in his 50s outshine his younger fellows.