Wear a dress shirt with charcoal wool dress pants for a truly smart outfit. Rounding off with dark brown derby shoes is a surefire way to add a carefree vibe to your look. This combo is a striking example 50-year-old guys can still very well draw compliments.
For an ensemble that's casually smart and wow-worthy, try teaming a dress shirt with khaki chinos. Take your outfit a whole other path by slipping into a pair of dark brown derby shoes. If you're worried about dressing age-appropriately, this getup is a safe bet.