This combo of a charcoal crew-neck t-shirt and charcoal skinny jeans is a safe go-to for an effortlessly dapper getup. Finishing with a pair of black suede chelsea boots is a guaranteed way to bring a dash of sophistication to this outfit. When leaves turn yellow and red and fall settles in, you'll appreciate how great this outfit is for transitional weather. So if you need dressing tips for guys over 40, this combo is a good example.