Red and Navy Gingham Shirt Smart Casual Chill Weather Outfits For Men After 40

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Grey Herringbone Flat Cap Navy Turtleneck Navy and White Polka Dot Pocket Square Blue Denim Jacket Navy Overcoat Red and Navy Gingham Long Sleeve Shirt White Chinos Navy Socks Black Leather Casual Boots

A red and navy gingham shirt and white chinos are a cool go-to pairing to keep in your closet. To give your look a more polished finish, add black leather casual boots to the equation. If you're wondering how you should dress as an over-40 man, this getup gives a fair idea.