An olive shirt jacket and a crew-neck t-shirt are amazing menswear must-haves that will integrate perfectly within your day-to-day casual arsenal. And it's a wonder what brown rain boots can do for the getup. When you're having one of those gloomy autumn days, sometimes only a neat getup like this one can get you to face the outside world. When it comes to casual dressing ideas for men in their fifties, this combination is a good look on most.