Black Overcoat with Tobacco Leather Casual Boots Smart Casual Chill Weather Outfits After 40

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White Vertical Striped Long Sleeve Henley Shirt Brown Herringbone Flat Cap Dark Brown Leather Casual Boots Charcoal Wool Dress Pants Navy Cardigan Black Overcoat

Consider wearing a black overcoat and charcoal wool dress pants if you're aiming for a clean-cut, fashionable ensemble. Bring a modern twist to this outfit by sporting tobacco leather casual boots. This combo proves that as a middle-aged guy, you have a vast array of dressing options.

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Grey Herringbone Flat Cap White Cable Sweater Black Overcoat Navy Jeans Brown Leather Casual Boots

If the dress code calls for a classy yet kick-ass look, team a black overcoat with navy jeans. Tobacco leather casual boots pull the ensemble together. A no-brainer for middle-aged gentlemen who are on a mission for age-appropriate clothing.