Hilary Duff's A Cinderella Story Is 20 Years Old — and Her Homecoming Gown Almost Didn't Happen (Exclusive)

When Hilary Duff walked down the stairs in A Cinderella Story's Halloween costume party scene in the 2004 film, audiences everywhere collectively gasped in delight at her gorgeous gown.

"Diner Girl" Sam, played by Duff, was a mostly unknown teen, but for one night, she got to be a princess in the princess-like ballgown — and she got to have her moment with her Prince Charming (aka Austin Ames, played by Chad Michael Murray).

But Sam's Cinderella gown that we've all come to know and love almost didn't happen, according to the film's costume designer, Denise Wingate, who revisited the movie for its 20th anniversary on July 16.

"I made so many versions of that dress," she tells PEOPLE with a laugh. "It was the biggest issue on that whole movie. I had the Walt Disney illustrated book of Cinderella, and I just remember the layers of pink and blue and iridescent, and I was trying to recreate that for the dress. It was a disaster. It looked awful. It looked like a big mishmash of color, and I kept trying to redo it, but it was awful."

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Wingate was getting down to the wire for filming the Halloween homecoming scenes — where Sam is going to meet up with her internet crush Austin for the first time in person — and desperately needed two of the same dress, so Duff and her stunt double would be ready to go. But all she had in her workroom were a few failed dresses that looked like "cotton candy" and not "classy" at all.

The week before they were going to film — when she says she was "literally in panic mode" — Wingate walked into a Monique Lhuillier bridal store and found the dress. And it was right off the rack.

"I knew the white was going to just pop," she says of -

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the bright bridal fabric of the wedding dress. "Hilary looked really beautiful, and that dress was the right choice. Not the pink and blue thing I was trying to make, and sometimes you don't realize that a piece doesn't work until after you film. It's better to find out before you shoot that it looked dumb. And that dress I made looked dumb."

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The other piece of the puzzle for that scene was Duff's mask, which had to be just right, because Austin couldn't know who she was — despite only a tiny portion of her face being covered. Wingate had to make sure Duff could see but that some of her face was still hidden. She's well-aware, though, that it was absurd for him not to know that it was her.

"You had to be able to see her eyes, but not to be able to see her too much, because the joke was for him to not know it was her," the Emmy-winning costume designer says while laughing. "How does he not know?! Isn't it obvious?!"

She says they made at least 15 different masks to try out before landing on the final one that still let her be "the star." It's delicate and pretty and covers just enough of her face to add mystery.

"It's a romantic scene, and you want to see her have this big moment," Wingate says.

In the end, Wingate found a mask shape that worked for the homecoming dance to trick Austin just enough, and of course (spoiler alert), Sam gets her happily ever after, à la Cinderella.

"The dress was perfect. Finding it was perfect, and it fit her perfect. It was literally the glass slipper."

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