Reach for a black shirt jacket and a black crew-neck t-shirt to create an interesting and modern-looking casual ensemble. Finishing off with a pair of black leather derby shoes is the simplest way to bring a dash of elegance to this outfit. Seeing as it is getting chillier every day, this outfit seems a viable option for in between seasons. So if you're looking for dressing tips for middle-aged gentlemen, this combo is an amazing example.