For rugged sophistication with a fashionable spin, you can rock a grey trenchcoat and charcoal dress pants. To bring out the fun side of you, introduce a pair of tobacco leather loafers to the mix. When it's one of those bleak fall days, sometimes only a cool look like this one can get you to face the outside world. This one is a modern yet age-appropriate pairing for a 60-year-old guy.