Plaid, Platforms & Perfection: Six Outfits from Clueless That Still Slay Fashion 30 Years Later

When examining the history of fashion in film, audiences tend to gravitate towards elaborate Victorian style outfits of period piece cinema or the immaculate dresses worn by Hollywood’s Golden Age. We overlook the complexity and difficulty of pulling off contemporary costume design, mainly due to our familiarity with the styles of the time. By undermining the significance of these outfits, we fail to see how they drive character development, and if done correctly become more timeless and culturally relevant than any fantasy couture.

This attention to detail and dedication to contemporary costume design created one of the most fashionable films in history [1]; a movie that not only used fashion as the driving force for the plot but had us totally buggin’ for a wardrobe makeover. That film was Amy Heckerling’s Clueless (1995), and when Cher Horowitz and her Beverly Hills gang stepped onto the big screen strutting one of the outfits by Polish costume designer Mona May, the world was saved from the army of baggy clothes, backward caps, and flannels of the grunge era.

Clueless kicked off a new wave of preppy minimalism: flaunting knee-high socks, plaid ensembles, and designer labels – becoming the blueprint for bold, playful, and totally fabulous fashion. With the 30th anniversary coming to theatres nationwide June 29 & 30, we scrolled through our computer closet app and picked out our six favorite fits that like still totally slay.

6. Amber’s Gym Fit

Amber Marien is known for her outlandishly vintage style – often juxtaposing or even rebelliously copying what Cher is wearing – and her gym uniform is no exception. With over-the-knee white socks and a lycra one-piece, Amber stands out from the rest of her classmates. This is reinforced by the fact she has stars on her outfit and is strutting another color other than black and white – red. By rejecting the unwritten dress code amongst the school, she is asserting not only her personality into the outfit but that she is the star.

The gym fit, along with her other distinctly Americana-inspired outfits, has left a lasting mark on pop culture. Icons like Katy Perry and Lady Gaga have clearly drawn influence from Amber’s daring fashion sense. She could strut out of the Clueless screen and onto the streets today, fitting right in with the bold, fashion-forward crowd. And let’s not forget, Cher, Dionne, and Amber helped pave the way for the athleisure trend, so you can thank them for making it a staple in our closets!

5. Tai’s Makeover

Tai Frasier’s journey from quirky outsider to a full-fledged fashionista is one of the most memorable parts of Clueless. Her transformation is marked by one iconic outfit: a maroon mini skirt with a matching long-sleeve shirt that signals her shift from awkward teen to confident, trend-savvy girl. This look is the quintessential 90s blend of preppy and grunge, designed to show how far she’s come since entering Bronson Alcott High School. It’s a look that symbolizes how Cher, despite her well-meaning but somewhat misguided efforts, has shaped Tai into someone who fits the Beverly Hills scene, while still allowing her personality to shine through.

Overall, the outfit has inspired countless teens on Tumblr and Instagram, who are replicating Tai’s unique charm.

4. The Calvin Klein Dress

Date night was never the same when Cher came downstairs to greet Christian in the now famous Calvin Klein dress. The soft fitted design is everything you would expect from a designer piece, but it’s the confidence that truly elevates it. Wearing the dress with minimal accessories – a precursor to Carrie Bradshaw’s “naked dress” – the simplicity speaks to her ability to look effortlessly chic. It also marks a turning point in her character arc, with Cher no longer just being a fashion forward teen, but a young woman beginning to understand the deeper layers of what it means to be fashionable, confident, and independent.

Like most of her outfits, the Calvin Klein dress has become a timeless staple in our fashion forward society. So much so that Alicia Silverstone reenacted the memorable father-daughter exchange before the date on her Tiktok – strutting the famous dress.

3. The Alaïa Dress

While fashion is basically a bonus character in the film, Cher’s Alaïa dress is the epitome of sophistication and high fashion in Clueless. Blending her youthful energy, fashion-forward thinking, and undeniable confidence, the dress was the perfect fit for the character – and the valley girl party/gas station robbery became a fan favorite scene.

At the time, Alaïa was not a household name in America, and the dress was hard to acquire, but both May and Heckerling wanted Cher’s style to be timeless – pulling from the runways in Europe instead of what was in the mall. Once the film was released, there was a wave of interest in Azzedine Alaïa’s work, and the brand became more common in America. The fact that Cher, a teen girl from Beverly Hills, was wearing a high fashion product was symbolic of how the movie elevated teen style into a space where fashion wasn’t just about trends. It was rare to see a teen character in the ‘90s wearing such a prestigious designer, and as a result the Alaïa dress cemented itself in pop culture.

2. Dionne’s Plaid Ensemble and Rose Hat

It’s hard to argue with the impeccable taste that Cher’s no-nonsense best friend, Dionne Davenport has. Every single one of her outfits not only complements Cher but has proven to be equally as timeless in a more colorful and adventurous way. One of her most memorable looks is her black-and-red plaid ensemble, complete with a crisp white blouse, cropped blazer, and a mini skirt that gave prep school a high-fashion upgrade. But the crown jewel of the look? Her oversized black hat adorned with a dramatic red rose—an accessory so unforgettable, it practically deserves its own credit in the film.

Taking inspiration from Audrey Hepburn’s look in My Fair Lady (1964) and kicking off the soft hat craze of ‘90s fashion, the fit perfectly encapsulates the polished yet daring style – something that Amber Mark wore alongside Sabrina Carpenter in a recent TikTok. Dionne’s ability to blend high drama with schoolgirl structure in this fit not only influenced her generation, but also famous designer Kokin – who helped create the hat alongside May for the film.

1. Cher’s Yellow Plaid Ensemble

Arguably one of the most influential ensembles in cinematic history, and a defining look for not only the changing landscape of ‘90s fashion but a permanent fixture in pop culture is the yellow plaid suite with a matching pleated skirt. The outfit is symbolic of high fashion with a Valley Girl twist, offering a timeless take on the ever-evolving Euro-fashion scene mixed with the quintessential school look. This idea not only complements the source material Clueless is based on – Jane Austen’s novel Emma – but modernizes it. So much so that director Autumn de Wilde used a yellow Victorian dress in the period piece retelling of the story, Emma (2020).

The unapologetically feminine look has become a regular Halloween costume amongst celebrities such as Kim Kardashian – alongside her daughter North West –, Sabrina Carpenter, and even Alicia herself recreating the iconic look for a super bowl commercial in 2023 [2]. In addition, Iggy Azalea and K-Pop superstar group Loon donned the trademark fit in their music videos “Fancy” and “love4eva.” Overall, it’s hard to pick a more iconic and contemporary influential outfit than the yellow plaid suite. It truly slayed and is still slaying fashion.

Plaid, Platforms & Perfection

From Cher’s iconic yellow plaid to Dionne’s fearless flair, each one of these outfits gave us a blueprint for bold, expressive, and completely unapologetic fashion that became staples of pop culture. So next time you’re staring at your closet thinking, “I have nothing to wear,” just ask yourself: What would Cher do?