The Most Iconic Fashion Moments in Cinematic History

The Most Iconic Fashion Moments in Cinematic History

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They are the moments that inspire designer recreations, cult followings, and fashion house campaigns decades later: the most iconic fashion moments in cinematic history. It’s a daunting task to narrow it down – doubtless there are dozens of pieces across decades of on-screen moments which make our hearts soar seeing the dress or that jacket. Alas, we’ve compiled a list of arguably the most iconic fashion moments, and bear with us as we’ll be using that word a lot, because these outfits should win an Oscar for how powerful they make whatever scene they appear in. 

That Little Black Dress: Breakfast at Tiffany’s (1961)

Image: Shutterstock

It would be a crime not to begin this list with Audrey Hepburn’s “little black dress”, which she wears as Holly Golightly in Breakfast at Tiffany’s. Perhaps the most iconic piece of clothing in all of cinematic history, this Hubert de Givenchy creation, designed specifically for Hepburn, would not only have a lasting impact as the pinnacle of sophisticated style but forever be a timeless symbol of New York City. Holly steps from that yellow cab in that cocktail dress to gaze at Tiffany and Co.’s windows, coffee and croissant in hand, the black frock cementing Hepburn as Givenchy’s muse and global fashion icon for the remainder of her life and beyond. Since then, there are countless recreations inspired by the original Givenchy design, notably Ariana Grande’s launch as the new face of the house of Givenchy, her Fall/Winter 2019 campaign channeling Hepburn in tight black frock and pearl accents.

Dolce & Gabbana Yellow Plaid: Clueless (1995)

Image: Today

Besides spotting the pairs of Blair Waldorf’s and Serena Van der Woodsen’s each October, Halloweens always have a Cher Horowitz clad in that utterly classic bright yellow plaid suit. In a 2020 interview with Vogue, lead actress Alicia Silverstone said that the grunge music genre that defined the ‘90s had an influence on the style in the film, and certainly that famously unique Dolce & Gabbana plaid skirt and jacket. It’s classic school-uniform essence with Cher’s agenda-driven confidence built in. When you see that yellow pattern, you see a ridiculously fabulous high school adventure.

A Historic Red: Outlander (2016)

Image: Us Magazine

It’s a moment when we all collectively gasp, as Claire Fraser (played by Caitríona Balfe) descends the grand stairs on a Paris eve, securing herself as a member of the beau monde and her 18th century peers. The time-traveling heroine dons woolen plaid and 1940s frocks throughout Season 1 of the wildly popular romance-historical fiction TV show, but nothing compares to designer Terry Dresbach’s creation for Season 2. Her team produced 10,000 costumes for this season alone, channeling influence of Balmain, Balenciaga, and Dior. But it’s the absolutely roaring red dress that has Claire immediately incandescent. It’s so simple in its appearance with no bells and whistles; instead, it’s dangerously daring, reflecting the description in the book of the front basically being a window down to her third rib. Obviously, Dresbach doesn’t take that literally, but still ditches the corset and embraces the classic ball gown of wasp waist and massive, billowing skirt, concluding the piece at fifteen yards of fabric. Can you say ooh la la?

Polka Dot Prom Dress: Pretty in Pink (1986)

Image: Hello Giggles

I mean, Andie Walsh herself is a designer, so a prom dress that she creates needs to be epic. You will remember the tension between classes as Andie tries to hide that she lives in the less ritzy part of town from love interest Blane McDonagh. So her prom dress would need to come down to homemade style. Luckily, throughout the movie Andie shows her resourcefulness of pulling together materials and sticking together pieces to create truly one-of-a-kind 1980s apparel. The movie’s costume designer Marilyn Vance said that instead of following the decade’s classic fashion staples she neglected to date anything specifically. That’s why the high-neck, polka dot piece is truly timeless. It can’t fit into a decade because it’s not supposed to. A symbol of authenticity, the prom dress like Andie is exactly who she is, beautifully creative, unlike any other, and capable of shattering societal norms to shine above the rest.

That Green Dress: Atonement (2007)

Image: Flickr

Impossibly daring, slinky as hell, and flowing like ripples in smooth water; Cecilia Tallis’ emerald green dinner dress, yes that green dress from Joe Wright’s adaption of Ian McEwan’s heartbreaking wartime novel, is the definition of momentous in the fashion world. This dress has hundreds upon hundreds of pages written about it. Its tempting slits and loose fit are still referenced by stylists today. Reflecting the intensity of the scene where the dress first appears, its fabric opens ever-so-slightly as Cecilia throws open the door to find Robbie (played by James McAvoy) on that sweltering summer evening before everything changes. The entirely open back and thin straps would have certainly raised sophisticated company’s eyebrows at the time (the moment taking place in a 1935 England), which reflects Cecilia’s bold and free-spirited style. That decade’s fashion for women saw dresses losing that tight, corseted silhouette expectation and continuing the 1920s flapper influence to find a straighter shape. Designer Jacqueline Durran followed those guidelines somewhat, taking considerable creative liberty to make the dress stand alone in its look, length, and colour 一 making it a truly unique piece. This dress will forever be symbolic of hot summer evenings, crackling romantic tension, and a most enticing plotline.

Sandy’s Leather Comeback: Grease (1978)

Image: CNN Style

It’s such a famous finale in cinematic history, made forever identifiable by the skin-tight leather pants, jacket, and bare-shouldered top on Olivia Newton-John. She had to be stitched into the black “Bad Sandy” number each morning filming the “You’re The One That I Want” scene, and when she glides in to emotionally destroy Danny Zuko (played by John Travolta), she proves she’s a bright-coloured dress and ponytail-wearing good girl no more. We like to imagine the cinema-goers cheered during the premiere. The outfit is featured on the official movie poster that still paints dorm room walls to this day (obviously, this movie is iconic). Turns out, the high waisted spandex pants were already a vintage get. Grease’s costume designer Albert Wolsky chose an almost 30 year old sharkskin piece from the ‘50s, which we can only imagine was more of a corset-feel than the usual comfort of a high waisted get-up.

Dancing Yellow in the Lamplights: La La Land (2016)

Image: Vulture

We can hear the first notes of that song – the one where Emma Stone (Mia) and Ryan Gosling (Sebastian) start to dance at twilight, the streetlights made into ethereal stage lights in the cityscape behind them. Costume designer Mary Zophres drew from 1930s influence, creating a flattering square neckline for Stone in the famed canary yellow. Swaying beautifully with Stone’s movement, the dress fits the character 一 a struggling actress fresh from a pool party, needing the flexibility to dance in the coming moonlight with a stranger if the opportunity arises. With a hand-painted floral design, the little yellow dress shines so brightly in the dim evening, a beam of light your eyes follow for the entire dance 一 and not sure to forget long after the scene is over.

On a New York City Breeze: The Seven Year Itch (1955)

Image: Wikipedia Commons

I think we’ve arrived at the most iconic moment: the Marilyn Monroe in New York City moment. it could never be pulled off by any other than the woman who is emblematic of the sexual revolution of the ‘40s and ‘50s. In 1954, Monroe stood atop a New York City subway grate and her white dress flew up freely above her knees. “Isn’t it delicious?” she famously says. The dress’s designer William Travilla thought nothing of the piece, which he referred to as “that silly little dress.” But Monroe was and is an undisputed icon of fashion, beauty, feminism, and confidence, and that halter-topped white dress along with her. On Lexington Avenue between 52nd and 53rd street, history was made. The image inspiration was borne from a similarly posed magazine cover seven years prior by photographer Sam Shaw, where it was revisited for the scene in The Seven Year Itch. An inspiration for body positivity and self love, we’ll gladly hand over first place to the Blonde Bombshell for the most beautiful, classic, and of course iconic fashion moment in cinematic history. 

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