Red Pocket Square Dressy Chill Weather Outfits After 40

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Clear Sunglasses Light Blue Dress Shirt Burgundy Pocket Square Brown Print Tie Grey Wool Waistcoat Grey Wool Blazer Grey Wool Dress Pants Brown Leather Casual Boots Black Leather Bracelet Black Leather Watch

Consider wearing a grey wool blazer and a red pocket square for a bold casual outfit that's also easy to wear. For a more elegant spin, introduce brown leather casual boots to the equation. This outfit demonstrates that as a 40-something gent, you have a vast array of styling options.