White and Red Check Dress Shirt Dressy Fall Outfits For Men After 40

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Brown Knit Tie White Check Dress Shirt Grey Check Wool Blazer Dark Brown Wool Waistcoat Olive Leather Zip Pouch Charcoal Wool Dress Pants Dark Brown Suede Chelsea Boots

Pair a white and red check dress shirt with charcoal wool dress pants if you're going for a clean, stylish ensemble. Take a more relaxed approach with footwear and complete this look with a pair of dark brown suede chelsea boots. As you can see, this combo is a really good pick, especially for weird transition weather, when the temps are dipping. A wonderful example for any man who's still figuring out how to dress age-appropriately while still looking stylish.