White and Navy 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

To look like a real dandy, consider pairing a white and navy check dress shirt with charcoal wool dress pants. To introduce a playful feel to this outfit, complement your look with a pair of dark brown suede chelsea boots. There's no better way to brighten up a gloomy fall day than a kick-ass outfit like this one. This getup proves that figuring out how to dress well as an over-40 man is quite manageable.