![Grey Derby Shoes with Shirt Jacket Outfits After 50: If the situation allows an off-duty menswear style, you can wear a shirt jacket and red plaid shorts. Round off your look with a pair of grey derby shoes to change things up a bit. This pairing demonstrates you can make a sartorial statement no matter your age.](https://cdn.lookastic.com/looks/shirt-jacket-crew-neck-t-shirt-shorts-large-57568.jpg)
![Blue Shirt Jacket](https://cdn.lookastic.com/blue-shirt-jacket-original-11480822.jpg)
![White and Blue Print Crew-neck T-shirt](https://cdn.lookastic.com/white-and-blue-print-crew-neck-t-shirt-original-4026913.jpg)
![Red Plaid Shorts](https://cdn.lookastic.com/red-plaid-shorts-original-486222.jpg)
![Grey Suede Derby Shoes](https://cdn.lookastic.com/grey-suede-derby-shoes-original-2413113.jpg)
![White Canvas Tote Bag](https://cdn.lookastic.com/white-canvas-tote-bag-original-8624896.jpg)
![Navy Baseball Cap](https://cdn.lookastic.com/navy-baseball-cap-original-614142.jpg)
If the situation allows an off-duty menswear style, you can wear a shirt jacket and red plaid shorts. Round off your look with a pair of grey derby shoes to change things up a bit. This pairing demonstrates you can make a sartorial statement no matter your age.