In a What Not to Wear first we turned the tables on a mother who nominated her own daughter! When Ann went to school the preppy look was fashionable. The problem is that was over thirty years ago — and this Orlando music journalist never grew out of it. Ann knows what's hot in the world of music, but when it comes to her wardrobe, she thinks a string of pearls and a polo shirt with her pleated shorts make her look sophisticated. Her friends and children think she looks old fashioned. Stacy and Clinton have to get Ann to give up her pearls and her matronly look and update her style, but it's hard for Ann to let go of a look she's had most of her life. And when it comes to her hair, she's hasn't changed her style since kindergarten — until she comes face to face with stylist Nick Arrojo. Makeup artist Carmindy also has to battle with Ann to get her to update her look.

Check out Ann's fashion rules, mannequins, shopping lists and makeover details!