A barn jacket and a long sleeve shirt are great menswear essentials to have in the off-duty part of your wardrobe. For a more sophisticated vibe, why not add a pair of dark brown leather derby shoes to the mix? Keep this look in your head come warmer weather, and rest assured, you'll save time crafting an outfit on more than one occasion. Dressing inspiration like this will help you remain incredibly fashionable at 40 plus.