For an ensemble that's sharp and GQ-worthy, make a grey herringbone wool blazer and blue plaid dress pants your outfit choice. Dark brown leather derby shoes pull the getup together. During winter, when warmth is crucial, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is a good illustration that you totally can stay cozy and remain equally stylish during winter. If you're not sure how to dress your age without giving up on style at 60 and beyond, this pairing is a goofproof option.