For a cool and relaxed ensemble, consider teaming a biker jacket with black jeans — these two pieces go pretty good together. Puzzled as to how to complete this ensemble? Wear a pair of dark brown casual boots to bump it up a notch. Keep this look ready to go when warmer days are here, and we guarantee you'll save a ton of time getting dressed on more than one morning. This combo illustrates that as an over-50 man, you still have a vast array of outfit options.