Dress to impress in a light blue dress shirt and charcoal wool dress pants. When it comes to footwear, go for something on the laid-back end of the spectrum by rounding off with tobacco suede desert boots. So as you can see here, it's a kick-ass, not to mention season-appropriate, outfit to have in your seasonal rotation. As you can see here, even after fifty you still have a vast array of dressing options.