For a casual and cool outfit, wear a black shirt jacket and a white crew-neck t-shirt — these two items play nicely together. Bring an extra touch of refinement to this getup by wearing tan suede loafers. Keep this look in your head come warmer days, and rest assured, you'll save a ton of time getting dressed on more than one occasion. All in all, a safe option when it comes to outfit ideas for 50-year-old gents.