He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right? It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.