A smart casual pairing of an overcoat and a gilet can maintain its relevance in a great deal of settings. Not sure how to finish off? Complement your ensemble with a pair of black leather casual boots to mix things up. With a look like this in your winter sartorial collection, you'll manage to keep warm and look stylish despite the below-freezing temps. If you're wondering how you should dress as a guy over 40, this ensemble is a good source of inspiration.