Just because one woman has her mother's looks, doesn't mean she needs her outfits too. Courtney Caldwell is an energetic, self-motivated financial consultant on her way up in the business world. Fresh out of college, Courtney's only 22 years old, which is just a few years older than most of her weathered wardrobe. Courtney literally got her style from her mother, since she sees clients while sporting her mother's old work outfits from the late 80s. Nominated by her friend at work, it's time for Stacy and Clinton to step in and teach this dated diamond in the rough What Not To Wear.