One of the most swoon-worthy moments from John Green’s novel might be when Hazel (played by Shailene Woodley) and Gus (played by Ansel Elgort) go on a date. While trying to stay true to the book’s description of Hazel’s dress (“this blue-print, flowy knee-length Forever thing”), LA-based costume designer Mary Claire Hannan also knew Woodley couldn’t sensibly wear a chipper sundress in Amsterdam during rainy weather in October. It was a quandary and, for a minute, she couldn’t solve it.

So, according to the Hollywood Reporter, just before boarding a flight to the Pittsburgh set, Hannan raced through the Beverly Center, one of L.A.’s most popular malls, on a hunt. With a little fashion fairy godmother magic, she came across a blue dress at Halston Heritage, purchased it, and pitched that dress and that dress only to the producers on set. They agreed that it was perfect. “I saw that dress and thought—that’s her!” Hanana told the Hollywood Reporter. The journey of Hazel’s date-scene dress is like a romantic roller coaster ride in itself, and while you stained your jeans with tears watching The Fault in Our Stars, you probably didn’t realize all the diligence and thought that went into the look.

Cinematic history tells us the relationship between costume and film is chock full of serendipitous stories, luck and unexpected choices just like this one. Here’s a quick case study on a few iconic film dresses and outfits with more to say than just “I’m pretty!”

The Atonement (2007)

The sad British romantic war drama itself may not bring jubilant memories, but costume designer Jacqueline Durran’s emerald green dress design was a big bright YES moment to fashion and film fans. Durran created the dress from scratch, intending to avoid the “scruffy, slumpy, and bumpy” styles classically adopted by upper-middle class familes during the 1930s. The green color was specially requested by director Joe Wright even though green in film is typically known to make film viewers uncomfortable (hence why Alfred Hitchcock dressed Tippi Hedren in a green suit in The Birds).

Pretty in Pink (1986)

If you look at your prom dress and cringe, you’re not alone; Molly Ringwald hated her prom dress in Pretty in Pink. (which was actually made from two dresses by costume designer Marilyn Vance. She told fans at a 25th Anniversary reunion that she kept all of the clothes from the film except the prom dress because she detested it so much. She added, “Now of course it’s the only thing I want. I love it. It’s so of that time and different from what everyone else was wearing. Maybe one day I’ll bid on it at Christie’s or something.”

Pretty Woman (1990)

Did you know the iconic red opera dress was supposed to be black? Marilyn Vance (yes she did BOTH movies!) shared with Elle magazine that the studio wanted the dress to be black, but her instincts told her otherwise. “Before the decision was made, we ended up having to create three different dresses. We took every color, lit it, and shot her. Poor Julia had to sit for so many color test shots for that one dress.” And apparently, the dresses manufacturer gets multiple requests every year from men to recreate the dress for their significant others!

Breakfast at Tiffany’s (1961)

French designer Hubert de Givenchy designed Hepburn’s opening look in Breakfast at Tiffany’s, but she didn’t end up wearing any of his original “LBD”’s in the film; the film’s dress was redesigned by Edith Head because Givenchy tried to show too much leg the first time around. Hepburn said about Givenchy, “His are the only clothes in which I am myself. He is far more than a couturier, he is a creator of personality.” This costume did more than just suit the character of Holly Golightly — it defined Hepburn’s elegant pixie look.

The Outlaw (1943)

Film director Howard Hughes custom-designed an underwire bra for the then up-and-coming starlet to wear during filming. Russell divulged in her 1985 autobiography that the bra was so uncomfortable, she secretly wore her own bra, padded the cups with tissue, and pulled the straps to push up her breasts. Sounds like Victoria stole her secret from Jane Russell.

Letty Lynton (1932)

Even in black and white, Crawford sparkled on screen in a white cotton organdy gown, puffed at the shoulder with some statement-making sleeves. If a dress could have a resumé, the “Letty Lynton dress” would be the most impressive. Designed by costume design icon Adrian (a.k.a. Adrian Greenberg) who created the costumes for The Wizard of Oz, the dress inspired Macy’s to create a ‘new look,’ and 500,000 replicas of the Letty Lynton dress sold nationwide. This was also the introduction to shoulder pads, and the growing impact of film on fashion in real life.

What are your favorite fashion moments in film history? Tweet and share your film muses with @HelloGiggles