For a casually classic look, pair a white dress shirt with shorts — these two items fit perfectly well together. Complement this ensemble with low top sneakers to immediately up the wow factor of your ensemble. A great example for any gentleman who's not sure how to dress age-appropriately.
This ensemble with a black overcoat and shorts isn't super hard to pull off and leaves room to more sartorial experimentation. For something more on the daring side to finish off this ensemble, complement your look with a pair of low top sneakers. An ensemble like this will make any 50-year-old gentleman look better than any of his peers.