![Navy Bomber Jacket with Red Plaid Shorts Casual Outfits For Men After 50: Pair a navy bomber jacket with red plaid shorts if you seek to look casual and cool without too much work. Balance out this outfit with a more sophisticated kind of footwear, such as these grey suede desert boots. Think you can't pull off cool casual dressing as you move into your 50s? This combo will prove you wrong.](https://cdn.lookastic.com/looks/bomber-jacket-long-sleeve-shirt-shorts-large-57438.jpg)
![Navy Bomber Jacket](https://cdn.lookastic.com/navy-bomber-jacket-original-3655991.jpg)
![Light Blue Long Sleeve Shirt](https://cdn.lookastic.com/light-blue-long-sleeve-shirt-original-2899599.jpg)
![Red Plaid Shorts](https://cdn.lookastic.com/red-plaid-shorts-original-486222.jpg)
![Grey Suede Desert Boots](https://cdn.lookastic.com/grey-suede-desert-boots-original-503460.jpg)
![White Canvas Tote Bag](https://cdn.lookastic.com/white-canvas-tote-bag-original-8624896.jpg)
![Navy Sunglasses](https://cdn.lookastic.com/navy-sunglasses-original-9639743.jpg)
Pair a navy bomber jacket with red plaid shorts if you seek to look casual and cool without too much work. Balance out this outfit with a more sophisticated kind of footwear, such as these grey suede desert boots. Think you can't pull off cool casual dressing as you move into your 50s? This combo will prove you wrong.