The good thing about WASP/Preppy style is that the clothes you wore when you were sixteen will still look good on you when you are sixty-five. Take this gentleman for example! His OCBD shirt and classic navy and yellow repp tie would look natural on a much younger gent, but looks equally good on this older gentleman. I love the fact that he leaves his tie undone, and his collar unbuttoned. I would not recommend making a practice of this, but he pulls it off somehow.