Opt for a black crew-neck sweater and a charcoal crew-neck t-shirt if you want to look casual and cool without exerting much effort. And if you wish to effortlessly step up this outfit with one single item, why not complement this outfit with dark brown suede casual boots? This one is an exciting choice when it comes to a neat look that will take you from summer to fall. An outfit like this will help any guy in his fifties outdo his younger fellows.