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prep/preppy comes from the term "preparatory school," which kind of gives you an inkling of its meaning. It suggests that someone is clean-cut, comes from a well-off family, and leans more towards the golf/tennis styles in terms of fashion. the stereotypical image would be khakis, collared shirt tucked in, plays one or more sports, no tattoos or non-ear piercings, listens to top 40, a good student, teacher's/parent's pet, etc. Abercrombie & Fitch is a modern take on "prep."
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