A grey trenchcoat and a white crew-neck t-shirt make for the ultimate casually classic ensemble. If you wish to effortlessly play down your ensemble with one single item, complete your ensemble with a pair of black and white canvas low top sneakers. This one is a viable pick when it comes to a kick-ass look that transitions easily into fall. This outfit demonstrates that even well into your 50s you still have a wide range of dressing options.