This relaxed casual combination of a black harrington jacket and a crew-neck t-shirt is extremely easy to put together without a second thought, helping you look amazing and prepared for anything without spending a ton of time combing through your wardrobe. And if you wish to effortlessly lift up this look with a pair of shoes, opt for brown leather chelsea boots. So if you're looking for dressing tips for gents in their fifties, this getup is definitely worth saving for later.