Clueless @ 25: The Best Costumes!
Sunday, July 19, 2020 at 10:36PM 
As previously mentioned in my "Emmas of Yore" miniseries, Clueless is one of the best cinematic adaptations of a Jane Austen novel. By modernizing the core narrative of Emma and stripping it of historical detail, Amy Heckerling was able to create a teen movie classic whose biting satire exists hand-in-hand with a sense of overwhelming affection for every character on-screen. Humor and romance are well-balanced, with the comedic element always taking precedence over the love story – as it should be when tackling one of Austen's prickliest and funniest novels.
That being said, to celebrate the 25th anniversary of Clueless' release, we're not going to focus so much on its genius screenplay or how it updates Regency-era social commentary to the Beverly Hills of the 1990s. Fashion is our concern this time around or, more accurately, we're exploring the costume design of Clueless. Since 1995, Mona May's colorful stylings have become as iconic as the screenplay's witty dialogues and, in a fair world, they might have even won the designer some well-deserved Oscar gold…
Before delving into any of the individual designs, we should clarify that Clueless isn't set in the real world, not quite. Heckerling's direction emphasizes an archness to the way these teens behave, and, through exaggeration, she created a caricature of reality that's as funny as it is grotesque. We may be dazzled by the glamour of these privileged teens, but we're also slightly horrified by their vapidity and complete lack of self-awareness. After all, the very construction of the movie calls attention to this strange dynamic when it has its heroine, Cher Horowitz, proudly proclaim how normal she is in voice-over while, on-screen, we watch her use a computerized closet to magic up an outfit for the day. And that's just the picture's opening.
Mona May's costumes walk the line between fashion and caricature, between escapist glamour and humorous exaggeration, just like Heckerling's writing and direction. Cher's first iconic outfit reflects that quite well, being, in essence, a glammed-up version of a schoolgirl's uniform whose bright yellow doesn't project the idea of sophisticated style so much as it labels Cher a fashion victim. The outfit is poppy fun, but it's also funny. It immediately defines the character's sunny disposition in the most obvious way possible and uses the plaid textile to draw a line that ties Cher together with countless other high school movie heroines. Look at Cher's plaid skirt suit and you'll see the ghosts of Heathers and a prelude to Lara Jean from To All the Boys I've Loved Before.
The rest of her wardrobe may vary wildly throughout the movie, but plaid is a recurring motif as are little details that suggest Cher's youth, like fuzzy sweaters, knee-high socks, flashy barrettes, and Mary Janes. As it happens with every Emma adaptation, we must understand that our heroine thinks herself more astute and mature than she really is, a character aspect that May's costumes brilliantly suggest without being too obvious about it. More importantly, perhaps, they do it without making Cher look like a clown. Like the rest of Clueless' satirical elements, the costumes may ridicule the superficial figures of the story but they never elicit our cruel mockery of them.
Of course, the genius of Clueless' wardrobe goes way beyond Cher's plaid suit. May's creations crystalize the teen fashion of the mid-1990s with great precision. In some regards, the costumes almost look like they were made for a period piece from a modern perspective. They highlight silhouettes and trends that, in retrospect, synthesize a specific time and place with astonishing immediacy. Looking at the girls in their black and white P.E. ensembles (complete with gold-chained purses and cellphone cases, as you do) or the parade of sagging jeans and bucket hats of the oft-disparaged high school boys and we see perfect encapsulations of style archetypes that now belong in the annals of fashion history.
Even when it comes to brand-named designers, Mona May was amazingly prescient. The shift dress Cher wears for one of her "dates" with Christian has become the ultimate symbol of Calvin Klein's minimalistic aesthetic, summarizing that brand's general approach to fashion and design with as much simplicity as wit. Though, again, the wonders of Clueless' costumes also extend beyond its ability to typify the fashions of 1995. The costumes also help define characters and narrative arcs, like Tai's evolution from grunge to preppy peppiness or Dionne's distorted mirroring of Cher (or is it the other way around?). Quite honestly, as much as I love our protagonist's wardrobe, I always end up being more drawn to her bestie's style. What's not to love about Dionne's fixation on vinyl trimmed garments and crazy hats?
In cinema, costumes can have many functions and tasks. They can be used to define a time and place, societal rules, and economic hierarchies. They may set the tone of scenes, whether by general style or the curated selection of a color palette. They may even define characters in ways the script can't and create visual narratives that run in tandem with the textual and performative story being told. Sometimes, they can just be used to dazzle or to horrify, to produce visceral reactions in the audience. The costumes Mona May conceived for Clueless do all that and more and that's why this is one of the best-costumed movies of its decade. I'd have given it the Best Costume Design Oscar of 1995, that's for sure.
Do you agree that AMPAS should have recognized the greatness of Mona May's designs? Also, what's your favorite outfit from Clueless?
Reader Comments (9)
The yellow and black plaid jacket and mini skirt is right up there in cinema history with Keira’s green dress from Atonement!!
Iconic film, iconic outfits.
The movie deserved much more recognition for Silverstone's performance (not even a Globe nod!), screenplay and costumes.
Some of my all-time favourite costume design - just brilliant and so fun! And although it is extravagant, it truly is, at least in my generation (early 20s), very influential on style.
I’m shocked it got no love from The Academy....and not even a Golden Globe nomination!
Still as fun, witty, and brilliant as it was 20 years ago!
I would have nominated it for
Best Picture (if there were more than 5 nominees)
Actress
Original Screenplay (according to AMPAS, it was deemed original and not adapted)
Costume Design
Original Song: “Supermodel” (Perfect song for the makeover scenes! Why was this song not a huge hit? Or even nominated? It was written for the film)
Agree on Silverstone being overlooked,it's 1 of those roles were you can't picture anyone else playing her.
The Calvin Klein dress is my favourite as it comes from my favourite scene,the boys were all dapper to.
I love the movie, have watched it a few times. My favorite line/retort is when Cher comes downstairs to say good night to her dad, before going out. He says something to the effect "what is that you are wearing". And Cher says "a dress". Dad says "Says who?" And Cher answers "Calvin Klein".
How much better would the Golden Globe line up for Best Actress Comedy if they went with these 5
Bullock,Silverstone,Kidman,Bening,Collette.
Simply one of my favorite movies ever and the costumes, as with all great movies, are an integral part of its appeal. The plaid suits are my favorites.
Cher was the fashion icon for a group of girls in my high school. The girl who sat next to me in calculus had a pretty good recreation of one of Cher's outfits.