If you feel more confident wearing something comfortable, you'll like this dapper combo of a dark brown shirt jacket and charcoal jeans. White canvas low top sneakers will add a more laid-back touch to an otherwise mostly dressed-up look. On not so cold days, you can sport this easy-to-transition outfit and look absolutely awesome. Those who are dubious whether you can still rock cool casual outfits as you pass the big 5-0, you have your answer.