You'll be amazed at how easy it is to get dressed like this. Just a blazer and black and white dress pants. When in doubt about what to wear when it comes to shoes, add a pair of dark brown leather monks to your look. So so as you can see, it's a seriously stylish, not to mention spring-friendly, outfit to keep in your seasonal rotation. And if we're talking fashion tips for over-50 gentlemen, this combo is perfect.