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- A New York socialite, deeply troubled and in denial, arrives in San Francisco to impose upon her sister. She looks like a million dollars but isn't bringing money, peace or love.
- As a fan of punk band, The Ramones, Jennifer has a wardrobe that needs to be sedated! At work, is dressing more like a maintenance worker than an urban professional. It's time for this playful, former headbanger to start dressing like an adult.
- Back in the 80s, pop-star Tiffany set trends with her hit songs and signature jean jackets. Longing for a change, Tiffany has nominated herself to find a new, modern style with the help of Stacy and Clinton - a first in What Not to Wear history!
- Elizabeth may be a loving wife and mother but her matronly style of floral shirts and mom jeans is embarrassing her family. Can Stacy and Clinton help this quirky mom find a sophisticated style that she and her family can be proud of?