Why not make a charcoal crew-neck t-shirt and charcoal skinny jeans your outfit choice? As well as totally comfortable, these pieces look amazing when teamed together. Feeling bold today? Mix things up a bit by rounding off with black suede chelsea boots. This ensemble is an exciting choice when it comes to a cool summer-to-fall outfit. So if you're on a mission for dressing tips for 40-something men, this outfit is a wonderful example.