This pairing of a grey turtleneck and charcoal dress pants is a solid bet when you need to look really classy. And if you want to effortlessly dress down this getup with a pair of shoes, why not add desert boots to this look? When staying inside on a frosty winter day is not a possibility, this outfit just might get you through the day. This outfit proves that passing the big four-oh is no reason to lower your sartorial standards.