So as you can see, looking on-trend doesn't take that much work. Pair a double breasted blazer with black chinos and be sure you'll look incredibly stylish. White athletic shoes are guaranteed to bring an air of stylish nonchalance to this outfit. So when summer is over and fall is setting in, this look is likely to become your go-to. And if we're talking casual fashion for 50-something guys, this outfit looks cool on almost anyone.