Dark Brown Leather Messenger Bag Cold Weather Outfits After 40

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Beige Turtleneck Dark Brown Leather Messenger Bag Brown Houndstooth Overcoat Black Leather Gloves Tobacco Chinos

For a laid-back and cool ensemble, consider pairing a brown houndstooth overcoat with a dark brown leather messenger bag — these pieces fit really well together. This ensemble shows that dressing cool as you go into your 40s is not that hard.