'Clueless' style: a fashion analysis of the best teen movie of all time

Dionne’s hat is interesting, because you can tie it to a wide range of music-inspired trends of the day, since people like Perry Farrell of Jane’s Addiction, Flava Flav of Public Enemy, Jay Kay of Jamiroquai and Linda Perry of 4 Non Blondes—among many others of the decade—became synonymous with dramatic, oversized, Dr. Seuss-style hats not dissimilar to this one. But you can also walk a little further out and liken it to the kind of dramatic head finery you see on some black women on Sunday mornings in a lot of African-American churches. That may seem like a stretch, but if you look at it from that perspective, it becomes part of a larger theme in Dionne’s costuming. Walk with us.

This is Dionne’s second style mode: wearing slightly parodic, ramped-up versions of African-American-inspired styles. The hair and beret are Reggae-inspired and the animal prints and low-slung tight pants are straight out of contemporaraneous hip hop. There’s this constant sense that she and her boyfriend Murray, who is always portrayed in slightly exaggerated (but not much) versions of ’90s rap-inspired styles (Timberland boots, Kangol hats, and pants falling off), are quite deliberately asserting themselves as representatives of black culture in this mostly lily-white and highly privileged setting. So is her crazy hat in the first scene just a crazy hat? Or is it another in a line of subtle ways she’s interpreting her cultural background in a place that’s somewhat bereft of it?

As for Cher, this is something of a variation on her first schoolgirl yellow, but with frilly touches and a slightly more grownup sense to it. In the first five minutes of the film, the throughlines of Cher’s wardrobe are established: bright or rich colors, plaids, and some variation on the four Fs: feathers, fuzz, fur, or frills, which all tend to highlight her fussy nature and princess-like attitude. There are, however, times when she eschews most of these elements, and those times almost always have to do with her interactions with boys.

When she’s with Josh, Cher will often dress in much simpler outfits than she wears at school, with fewer colors, prints or embellishments. In fact, black and white largely become her go-to colors whenever she’s home. This sheer black top and oversized cross pendant is a sort of ‘90s goth-lite by way of Beverly Hills, just as Josh’s plaid shirts evoke a grunge-lite vibe. Note that even here, her outfit has a frill at the sleeve.

Black-and-white costuming also comes into play in this pivotal scene:

We’re introduced to Tai in the very latest in 1995 stoner wear, which really isn’t all that indistinguishable from a lot of grunge wear: an oversized plaid shirt over a t-shirt. It’s a look that would render her practically invisible against the high-fashion runway that is Bronson Alcott high school. Or it would have, if costume designer Mona May didn’t make the smart decision to dress everyone else in the scene in black, white and gray. In a movie exploding with plaids (reportedly more than 50 plaids were used), it’s notable that, while everyone is wearing a distinct and noticeable costume, no one is wearing plaid. In an ironic twist, it’s the one time it signals someone as an outsider in the entire film.

Cher and Dionne take on Tai as their latest project and subject her to a makeover, the results of which are to render her pretty much indistinguishable from Cher and Dionne. None of the three girls are dressed exactly alike, but all of them are working in that same “schoolgirl” mode of short skirts and tights. Tai doesn’t come from an affluent background like the other two girls, so her costume is slightly plainer (no collar on the shirt, full tights instead of the sexier thigh-highs, a more muted color scheme).

Tai will slowly assert herself more in her costuming throughout the film, but the point of this shot and these costumes is to show her as a member of Cher and Dionne’s tribe.

By the way, we simply have to stop for a second and pay special attention to Amber, who is probably the most memorable of the secondary characters. That’s almost entirely due to her wardrobe, which manages to look outrageous even in the sea of eye-popping costumes on display in this film. Note how all her looks, though clownish somehow, tend to reference aspects of Cher’s and Dionne’s styles: the marabou feathers, the animal print fake fur, the obnoxious hat, the braids. “Ambular” is the ultimate wannabe.

In the party scene, Cher and Tai are together in almost every shot. Their matching reds point to their new bond (and reference the fact that it’s a Christmas-themed party), but the differences in how that red is executed says something about each girl. Cher doffs her fussy, feathered Alaia jacket for the scene, choosing to present herself in a stark and sexy red party dress. Tai, on the other hand, is all bouncing ringlet curls and dangly choker and mixed patterns, reflecting someone who’s fidgety and nervous in comparison to the confident Cher. But when her fortunes change and she finds herself stuck outside the Liquor Circus past curfew and with no way to get home, suddenly Cher looks silly, pampered, ridiculously out of place, and vulnerable. The Alaia was one of two name-checked designer outfits; the other was the Calvin Klein dress she wears on her first date with dreamboat Christian.

Cher’s white dress is somewhat similar to her red party dress, but instead of covering it up with something fussy and feathered, she opts for a sheer trenchcoat, which gives off a much more coolly sophisticated modern-sexy vibe, and helps set her off against Christian’s black-dominant retro style.

We should note some things about Christian’s style here. We called it “retro,” but his high-waisted pleated pants and cropped jackets, while calling back to decades like the ‘40s and ‘50s, were also very much in style in 1995. It’s easy to see how the character is referencing the iconic styles of men like Frank Sinatra or Dean Martin, but you have to remember that 1995 was also a period when Chris Isaak was at the top of his pompadour’d game, while wearing a whole lot of pleated pants, tight black tees and cropped jackets.

In other words, like the nods to grunge, goth and hip hop styles in other characters’ costumes, Christian’s retro Rat Pack-inspired looks were tipping their hat to current musical trends. Twenty years later, the character’s gayness may seem obvious to us, but aside from his total disinterest in doing anything but watch Tony Curtis movies with Cher, there was little about his costuming that signaled it to the audience, which was a particularly smart, not to mention open-minded, choice. This was not, after all, the best time for nuanced, un-stereotypical depictions of gay people in pop culture.

Back to Cher: Note the jeweled barrette in her hair. Put a pin in that, because we’re coming back to it.

Like the red party dress, the white CK also serves to highlight the differences between Cher and the skittish, unsophisticated Tai, who is dressing less like Cher and Dionne, but still a far cry from her initial stoner-wear. You can see this as an example of her journey trying to figure out who she is in this crowd. It’s not a coincidence that this ensemble is highlighted over and over again in this scene, showing the many ways she fusses with it to make it more acceptable somehow.

The white dress was for Cher’s first date with Christian, but when she wants to really get his motor running (bless her naive heart), she goes back to party red and ramps up the sex appeal:

This really isn’t all that dissimilar to the white CK dress or the other red party dress she wore, except this one is flimsier and has some movement to it, giving a sense of both comfort and sexiness. Like her first date with him, she sports an eye-catching barrette, but this time she added a ton of makeup, in a doomed effort to seduce him.

When she’s alone with Josh, however, she tends to strip away any attempts to project sophistication, sexiness and confidence and literally lets her hair down— then puts it back up in a collection of cheap plastic barrettes and hair clips, as opposed to the more elaborate, expensive and bejeweled ones she wore with Christian. It’s modest and low-key and not meant to impress anyone. She says as much in the voiceover for this scene, noting how her socializing ensembles are “so binding.” The lavender color is soft and vaguely romantic; pastels are associated with romance in this film, as we’ll see later. But they’re also associated with personal growth (again, as we’ll see later) and this scene foreshadows where Cher’s journey is going to take her.

But first, Cher has to go through some painful revelations that force her to grow up, and she does all of that in a series of scenes wearing one very noticeable costume—the one we call the Angel-Virgin look:

And it is, by far, the fussiest, silliest, most ridicu-fabulous getup she wears in the entire film. It’s got the cropped baby sweater, the sheers, the ruffles of so many previous costumes. It’s childlike, virginal, and prissy to an absurd extent. It highlights exactly what this portion of the film is about: a moment of growth and revelation following intense disappointments, like failing the driving test and fighting with Tai over Josh. At the end of the sequence she comes to the major revelation that she is, in fact, in love with Josh, the suddenly flowing, glowing fountain providing a perfect backdrop as she goes from being a girl to a woman in one moment. Metaphorically, of course. (At this point, she’s still technically a virgin who can’t drive.)

After this revelation, her costumes all change dramatically and fairly consistently. You see, Cher is grown up now. Grown up and in love. And in the world of Clueless, that means sensible ensembles and TONS of pastels.

Her entire wardrobe suddenly changes almost exclusively to romantic pinks and lavenders as she tries to make herself into a better person, a person worthy of Josh. There are no frills here, no ruffles or feathers, no plaids or thigh-highs, no bright or rich colors. Pastels—and especially pinks—are not just the colors of romance for Cher, they’re the colors of maturity and growth as well.

And what better way to illustrate that than to have her in a pale pink bridesmaid’s outfit, catching a bouquet and kissing her true love? She could only find love through her own growth and maturing process, and in the end, she stands with her man, dressed more like a grown woman than at any other time in the film. Contrast her bridesmaid ensemble with Dionne’s, which is much trendier and more youthful.

This final bit of costuming illustrates why Clueless has had such long-lasting impact and has inspired fond memories for an entire generation of viewers. Clueless isn’t a film about vapid mean girls or trendy fashion or even about young women pinning all their hopes and self-esteem on finding love. It’s Cher Horowitz’s coming-of-age story, plain and simple.

Tom Fitzgerald and Lorenzo Marquez blog at TomandLorenzo.com, and are the authors of Everyone Wants To Be Me Or Do Me.