White and Red Check Dress Shirt Chill Weather Outfits For Men After 50

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White and Red Check Dress Shirt Dark Brown Sweater Vest Dark Brown Barn Jacket Grey Wool Dress Pants Dark Brown Suede Desert Boots

Go all out in a white and red check dress shirt and grey wool dress pants. Balance this ensemble with a more laid-back kind of footwear, like this pair of dark brown suede desert boots. The ability to sport getups like this is one of the benefits of being middle-aged.

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Clear Sunglasses White and Blue Check Dress Shirt Navy Tie Navy Sweater Vest Navy Duffle Coat Navy Suit Navy Socks Black Leather Brogues

This pairing of a white and red check dress shirt and a navy duffle coat is a real life saver when you need to look stylish but have no time to plan a look. Add black leather brogues to the equation and the whole look will come together. Interested in dressing tips for gentlemen over 50? This combo is pretty inspiring.