Clothes on Film is a series in which we explore iconic looks from film and television that have stayed in our minds years after they first hit the silver screen.
A Cinderella Story  follows Sam Montgomery (Hilary Duff), a quiet high-schooler who lives with her—evil, of course—stepmother and stepsisters after her father died in an earthquake in their home in the San Fernando Valley. It’s a deft reimagining of the classic tale for the Hilary Duff generation.
Desperately hoping to attend college far from her family, Sam applies to Princeton. She joins a chatroom of other hopeful Princeton Tigers, and forms an online relationship with—unbeknownst to her at the time—her high school’s star quarterback, Austin Ames [Chad Michael Murray]. He invites her to meet him at the school’s masquerade Halloween dance where she makes a grand entrance in a gorgeous gown. Before Sam can reveal her identity to Austin, she has to leave, dropping her cell phone, the millennial glass slipper, as she scurries away.
The film’s costume designer, Denise Wingate, originally had a different vision for Sam’s dress, but ultimately went for a color and silhouette that was—much like we regard A Cinderella Story—an instant classic.
DENISE WINGATE: A Cinderella Story is a rags to riches story. I really liked the script and I liked Hilary Duff—she’s super sweet. Sam was a bit of a tomboy, but she was also confident. I think that mix resonates with younger girls today and that’s why these movies hold up. There may be a man in the picture, but there’s something about being independent and not needing that. She had a simple look. I kind of dress like that now—I have my Converse, my jeans, and a plain T-shirt. I’m a pretty understated person. But everything else about that movie was completely over the top, with the step-sisters, Fiona [Jennifer Coolidge], and the masquerade ball, which was fun. But Sam was the one grounded in reality and it’s about her, it’s about her journey.
When we were first trying to figure out Sam’s dress for the ball, I was harkening back to the original Cinderella, using all of those colored layers with this iridescent blue fabrics like you’ve probably seen in the Disney cartoon, and it just didn’t work out. I wanted it to be this colorful thing but after we camera tested it, it ended up looking like a mish-mash. So we went for something more classic, almost like a wedding dress, and just this beautiful vision of white. It was a Monique Lhuillier dress and it ended up being perfect. And for the mask … we made 12 different masks—there’s a lot of trial and error to get it right when you’re dealing with a statement outfit.