This combo of a dark purple cardigan and a dress shirt is a mix between elegant and casual. Let your outfit coordination expertise really shine by complementing this outfit with black leather derby shoes. During the colder months, when functionality is critical, it can be easy to surrender to a less-than-stylish getup in the name of convenience. But this getup is a stark illustration that you can actually stay comfy and remain equally stylish in the colder months. This combo illustrates that dressing cool as you step into your 50s is quite manageable.