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In this challenge, Maddy shops as the preppy contestant while Cilla represents the nerdy side for back to school. They start at Starbucks, where Maddy enjoys iced coffee and Cilla opts for hot coffee.

She then promptly ordered a copy of The Official Preppy Handbook, Lisa Birnbach’s classic 1980s survey of WASP codes and culture, for everyone in her department. They followed its tongue-in ...