You'll be amazed at how very easy it is to get dressed this way. Just a white and navy vertical striped dress shirt married with a multi colored houndstooth overcoat. For a more polished touch, why not introduce a pair of dark brown leather tassel loafers to the equation? We love that this outfit is great when chillier weather hits. If you're wondering how you should dress as an over-40 man, this combo is a good source of inspiration.