![Tobacco Casual Boots with Henley Shirt Smart Casual Chill Weather Outfits For Men After 50: For a cool and casual look, try pairing a henley shirt with white jeans — these pieces go really cool together. To bring a bit of zing to this getup, complete this look with a pair of tobacco casual boots. An outfit like this will help any man in his fifties outdo his younger fellows.](https://cdn.lookastic.com/looks/shirt-jacket-sweater-vest-long-sleeve-shirt-large-57553.jpg)
![Olive Print Shirt Jacket](https://cdn.lookastic.com/olive-print-shirt-jacket-original-11480814.jpg)
![Navy Sweater Vest](https://cdn.lookastic.com/navy-sweater-vest-original-11417278.jpg)
![Blue Chambray Long Sleeve Shirt](https://cdn.lookastic.com/blue-chambray-long-sleeve-shirt-original-359370.jpg)
![White Henley Shirt](https://cdn.lookastic.com/white-henley-shirt-original-2598801.jpg)
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![Brown Suede Casual Boots](https://cdn.lookastic.com/brown-suede-casual-boots-original-11313162.jpg)
For a cool and casual look, try pairing a henley shirt with white jeans — these pieces go really cool together. To bring a bit of zing to this getup, complete this look with a pair of tobacco casual boots. An outfit like this will help any man in his fifties outdo his younger fellows.