This combination of a beige double breasted blazer and blue chinos crosses the divide between dressy and off-duty. Hesitant about how to finish off? Introduce white leather low top sneakers to the mix to spice things up. So as you can see, it's extremely easy to look seriously stylish and stay warm when cooler weather comes, thanks to this look. Those who are curious how to dress stylishly well into your 50s, you have your answer.