If it's ease and functionality that you appreciate in an ensemble, marry a harrington jacket with jeans. You could perhaps get a bit experimental on the shoe front and class up this look by rounding off with a pair of navy suede loafers. When it comes to dressing for weird transition weather, nothing beats a killer getup that can take you from season to season. Interested in dressing tips for middle-aged gentlemen? This ensemble is great inspo.