Top 10 Iconic Fashion Moments in Film

To be clear, this is not a list about fabulous, historically accurate, dramatic costumes in film. This list encapsulates the most memorable moments of fashion captured on camera that have lingered in our minds and pervaded our collective consciousness. These clothes have endured the test of time and become a part of pop culture as we know it.

10. Sex And The City – The Movie

The FIRST one, obviously. From the array of wedding gowns Carrie parades about in (hellooo Vivienne Westwood), to the 80s delights that each of the ladies model, to the return of the iconic little tutu, the first SATC film did us proud. Like…it’s problematic as hell and I could spend an eternity analysing the treatment of Miranda’s marriage dissolution compared to Carrie being left at the alter (AND I WILL – Revisionist Series coming soon!), but at least the clothes were there. Which is more than you can say for the second film…but that was a shitfest in ways that I could never wrap up in a brief paragraph. Gimme a rosé and settle in for a long chat if you’re really interested in my thoughts on that dumpster fire from hell. Also I still remember how distinctly happy I felt that they moved away from Manolos in this film and had Carrie rocking PLATFORMS and GLADIATOR SANDALS and LOUBS in this one. It felt like such a magnanimous departure to me back then. I was young.

9. The Devil Wears Prada

Everybody loves a fashion montage and this film delivered in spades. Andy’s thigh-high leather Chanel boots would have been enough to get on this list, but add to that the perfect Calvin Klein jersey dress, the Yigal Azrouel ivory angora coat, the Galliano black evening gown… Perfect. All of it. And that’s just Andy’s wardrobe! Miranda takes it an even higher level. Heavennnn.

8. Grease

Sure, it’s all a fantasy. But tell me you can’t immediately recall every outfit from every scene of the entire movie. NOPE, SHUT UP, YOU CAN’T, BECAUSE IT’S IMPOSSIBLE. It’s all vividly iconic and the skintight black finale is in a world of it’s own. I mean, shit, Olivia Newton-John. What even is that waist?!

7. The Great Gatsby

Is it fair to say that the film itself inspired the never-ending stream of Gatsby-themed costume parties throughout the Western world? Was it the book itself? Was it the 20s as a whole that spawned yeeeaaaaars of flapper-themed dress-up parties? It’s hard to imagine the film didn’t ignite something in the greater consciousness of Earth. We’ve all been invited to one in our lives. Shit, it’s probably one of the most common go-to costumes no matter WHAT the theme. TV characters? “I’m someone from Boardwalk Empire…” Sparkles and diamonds? Bedazzled flapper and headband. Iconic couples? Gatsby and Daisy. The list goes on. Robert Redford and Mia Farrow DEFINITELY had an impact on this phenomenon, and the film is still a visual delight to take in. But I, for one, am sick of the Gatsby theme. Not forever…just, for a while.

6. The Seven Year Itch

Marilyn Monroe. White Dress. Air vent. ‘Nuff said.

5. Pretty Woman

Vivian’s red floor-length dress in ‘Pretty Woman’, which immediately takes her from hooker to high-class girlfriend, the polka-dotted day dress/hat combo at the polo, THE THIGH-HIGH BOOTS AND JUMPSUIT…! The list goes on. And even without the supporting imagery, I bet you can immediately conjure the visuals in your mind from these simple little words.

4. Contempt

3. Annie Hall

Slouchy trousers, buttoned vests, white oversized shirts, ties… ‘Annie Hall’ was groundbreaking in making man-style lady clothes a thing. It also cemented Diane Keaton’s cool status forever and ever, even if she does make films like ‘Because I Said So’ now. Also – have you seen her Instagram? It’s off-kilter whack-job perfection.

2. Breakfast at Tiffany’s

No DUH. Little black dress, pearls, Ray-Bans…what kind of world would this be without these particular items? Non-existent, that’s what. Audrey Hepburn as Holly Golightly is perhaps the most iconic female character ever to grace the silver screen. Whether she’s rockin’ the LBD or the perfect trench, she embodies style and sophistication that any lady can imitate or be inspired by. Which we will continue to be, for generations to come, forever and ever, always, as long as we wear clothes.

1. Clueless

Okay, so it wasn’t exactly representative of 90s fashion. Maybe we didn’t walk around in knee-high white socks, silver mary-janes, black-and- white checked mini-skirts and see-through white shirts thrown over the top (my fave, see below)…but my God, after we saw this film, weren’t we dying to?! Cher Horowitz’s outfits and revolving wardrobe have become firmly entrenched in pop culture. Her ensembles created a fun, escapist aesthetic which is now indelibly iconic. Bizarre as her clothes may have been, it just feels right that a beautiful sixteen-year- old girl can prance around in a head-to- toe yellow tartan outfit one minute and a skin-tight red Alaia the next. Even if it’s only on film.