For an ensemble that's very simple but can be manipulated in a variety of different ways, try pairing a turtleneck with olive chinos. Finishing with navy leather casual boots is a fail-safe way to introduce a little flair to this look. Keep this look in mind come warmer weather, and we promise you'll save a lot of time racking your brain for what to wear on more than one occasion. As you can see, as a guy over 40, you have a wide range of outfit options.