Why not team a navy wool shirt jacket with navy check chinos? As well as super practical, both items look awesome when paired together. For times when this look looks too dressy, dial it down by rocking white canvas low top sneakers. So as you can see, it's very easy to look seriously stylish and stay snug when colder weather arrives, thanks to this look. And if we're talking casual dressing ideas for maturing gentlemen, this combination is a good look on almost any gentleman.