Pairing a parka with grey ripped skinny jeans is a savvy option for a casual outfit. To introduce some extra flair to your ensemble, finish off with black and white athletic shoes. In the winter months, when warmth is prized, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look proves that you totally can stay snug and remain equally stylish in the winter months. How's that for fashion inspiration for casual dressing in your fifties?