When it comes to timeless class, this pairing of a white vertical striped double breasted blazer and white dress pants is the ultimate look. Grab a pair of brown leather tassel loafers to instantly kick up the cool of this getup. If you're racking your brain for a season-appropriate look, this one is a savvy option. This combo proves that figuring out how to dress stylishly as an over-60 man is totally doable.