A tobacco crew-neck sweater and khaki ripped jeans are indispensable menswear items to have in the casual part of your wardrobe. You can get a bit experimental on the shoe front and spruce up your ensemble with a pair of brown leather derby shoes. When spring is in full effect, you'll love this getup as your uniform for unpredictable spring weather. This combination demonstrates that even well into your 50s you still have a wide range of sartorial options.