For comfort dressing with a modern finish, try pairing a yellow vertical striped short sleeve shirt with black chinos. Want to dial it up in the shoe department? Add a pair of olive velvet loafers to this outfit. So if it's a super hot summer afternoon and you want to look dapper without exerting much effort, this outfit will do the job in next to no time. A practical illustration of how to dress stylishly as you reach your 50s.