Consider wearing a white and navy print crew-neck t-shirt and navy jeans if you're on the lookout for an outfit option that conveys urban style. A trendy pair of dark brown leather casual boots is an effortless way to bring a touch of sophistication to your outfit. There's no better way to brighten up a dreary fall afternoon than a cool getup like this one. And if we're talking casual dressing ideas for over-50 guys, this ensemble looks cool on most.