For a look that's street-style-worthy and effortlessly smart, try teaming a charcoal blazer with navy jeans. For something more on the sophisticated end to complete your ensemble, introduce a pair of white leather oxford shoes to your getup. During the winter months, when functionality is essential, it can be easy to settle for a less-than-stylish look. This look, however, is a practical illustration that you can actually stay warm and remain stylish during the winter months. So if you need style ideas on how to dress as you go into your 50s, this ensemble is ideal.