For effortless style without the need to sacrifice on comfort, we love this pairing of a dark brown shawl cardigan and blue jeans. When it comes to shoes, complement your ensemble with a pair of dark brown leather casual boots. During the winter months, when warmth is top priority, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a shining example that you totally can stay comfortable and remain equally stylish in the winter months. This one is a nice and age-appropriate pairing for a gentleman in his fifties.