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The Preppy Handbook
The Preppy Handbook is a book whose history we will get into if you haven't heard of it. What I think of are like cable knits, pearl earrings, intentionally slightly unraveled hems and edges of things. LL Bean, of course, especially the Bean Boot. Puffy vests, down vests even, are in there if you're in like Mayan or something. The canon of what Preppy is constantly expanding too.