Why not reach for a white and black polo and grey sweatpants? These items are very practical and will look amazing worn together. Finishing with a pair of low top sneakers is a simple way to introduce a little classiness to your ensemble. So as you can see, this ensemble is a really savvy choice, especially for in-between weather, when the temperature is starting to drop. When it comes to casual dressing ideas for 50-something gentlemen, this getup looks cool on almost anyone.