For an outfit that's super simple but can be smartened up or dressed down in a multitude of different ways, wear a blue blazer and dark brown chinos. Loafers will infuse a dash of elegance into an otherwise mostly dressed-down getup. With a look like this in your winter sartorial collection, you're guaranteed to stay snug and look stylish despite the below-freezing temperatures. Wondering how to dress age-appropriately as you move into your 40s? This ensemble is the perfect answer.