When I was eighteen, I received four copies of The Preppy Handbook for my birthday. I received another five for Christmas. Each time, the gift giver wrote on the card, "This is so you!" I didn't see the connection. Or perhaps I refused to recognize it. My parents were dismayed at the book. "It's a celebration of mediocrity and banal people," they said (mediocrity said with a short "e" as in red).
But there was something in there that seemed so "them." Perhaps it was the boat models in the dining room. Or my stepfather's white dinner jacket that I used for my prom. He wore it on a teenage tour of all the Debutante balls on the west coast in 1960. I had to admit that my family tree was like the "joke" tree in The Preppy Handbook (although my mother's half ends up at Jamestown; those Mayflower people were late in the game). And, unfortunately, a gang of relatives were in the "Pantheon" section.
By the time I was at CalArts I was as far from "preppy" as one could get. Or so I thought. I bought black jeans and dark colored shirts. But people still said, "You're so cute and preppy." It was a lost cause. No matter how hard I tried to be cool I ended up looking like I was visiting from Connecticut in 1955.
The nice thing about getting older is not caring what others think. I finally gave in and accepted that I liked the same clothes that I wore when I was a child. I didn't need to worry about being cool and not "preppy." The issue here is that my style goes in and out of fashion every twenty years or so. I'll look quite fashionable for awhile and then super un-cool for a decade. I buy clothes in triplicate so when Sperry stops making blue sneakers I will still have new ones in a box. But let me make this clear, the pants with little whales or tennis rackets are stupid. No matter what anyone says.