As you can see, looking casually classic doesn't take that much work. Just try teaming a charcoal crew-neck t-shirt with charcoal dress pants and you'll look awesome. And if you want to instantly step up this ensemble with a pair of shoes, why not introduce a pair of black leather chelsea boots to the mix? This one is a viable pick when it comes to a stylish summer-to-fall transition outfit. And if we're talking dressing ideas for 40-year-old gents, this outfit looks great on most.