This combo of a cardigan and a dress shirt is great for semi-casual events. Don't know how to finish off this ensemble? Rock a pair of navy leather derby shoes to ramp it up a notch. During the winter months, when functionality is a must, it can be easy to surrender to a less-than-stylish look in the name of functionality. But this look is a practical illustration that you can actually stay toasty and remain equally stylish in the winter months. This combo shows that moving into your 50s is no reason to lower your fashion standards.