So as you can see, it doesn't take that much work for a man to look sharp. Try teaming a grey blazer with a black turtleneck and you'll look incredibly stylish. And if you need to instantly bump up this ensemble with one single piece, why not complement this outfit with a pair of black leather derby shoes? So if you're on the hunt for an outfit that's seriously stylish but also entirely spring-ready, this just might be it. Outfits like this have a sophisticated air that befit gentlemen in their fifties really well.