When hopeful fashionista Meg Julliard must return to her hometown of Chicago to manage her late-father’s apartment building, she thinks her dreams of making it in the fashion business are over. Ellie Wade, one of the building’s longtime residents, is also not feeling the Christmas Joy this year. She is preparing to move into a nursing home (reluctantly), and is in the process of sorting through her belongings to downsize. But there's one dress she hesitates to pack up as it represents both the best and worst night of her life. Ellie and Meg strike up an unlikely friendship and the story of Ellie's dress comes out. Ellie gifts the gorgeous dress to Meg, hoping that it will bring her more luck, on the condition that she wear it to the building's Christmas party. The dress and the magic of the holiday season helps both Meg and Ellie find their own happy endings.