For a look that's pared-down but can be dressed up or down in a variety of different ways, opt for a blue double breasted blazer and white chinos. Blue canvas espadrilles will bring a carefree vibe to an otherwise mostly classic ensemble. This combo isn't a hard one to score and it's summer-friendly, which is important when it's super hot outside. With a look like this, any guy in his fifties is bound to put any younger dude to shame.