For comfort without the need to sacrifice on style, we love this combo of a dark green crew-neck sweater and grey chinos. Dark brown leather desert boots act as the glue that brings your outfit together. While it can be a bit of a challenge to look stylish on extra cold days, it's outfits like this that prove it's quite doable. Those who wonder whether you can still rock cool off-duty style as you go into your 50s, you have your answer.