“Preppy” was not something you wanted to be when I was in prep-school. Maybe it would have been if this was the style preppy kids were wearing then. Too many layers of popped-collar pastel polos and bottle-opener reefs for me.
As you ogle the style of that time, imagine yourself in one of those rooms.
Everyone is smoking, the air is thick with nicotine. You are wearing a wool sweater and itchy wool pants, silk socks and leather shoes. Your hair is oiled down with Brylcream. If it is summer, there is no air conditioning. If it is winter, the radiator will burn your hands.