At 24 years old, Ariana just got the promotion of a lifetime. She is about to move to Chicago to become the head of marketing for her sister's start-up company, but her closet of old and worn-out clothing will not make the right impression. Tim and Gretta set out to sway Ariana from her ingrained belief that growing up with a single mother, clothes have to fall apart before you replace them. It is time for Ariana to learn that some clothes are worth the investment. Fashion help from: Fashion designer Angel Sanchez and makeup artist Gordon Espinet of MAC Cosmetics.