Since its 1995 debut, cult comedy Clueless has been responsible for many things. Chief among them: launching the careers of Alicia Silverstone, Brittany Murphy, and Paul Rudd and spawning some of the most oft-quoted lines from the ‘90s (“As if!”, “You’re a virgin who can’t drive,” etc.). Very loosely based on Jane Austen’s novel Emma, the Amy Heckerling-directed film follows Cher Horowitz (Silverstone), a rich and popular Beverly Hills high-schooler, as she befriends a clumsy new student Tai (Murphy), conducts makeovers, and plays matchmaker with varying degrees of success — all before realizing her love for her ex-stepbrother Josh (Rudd).
But perhaps Clueless’ biggest legacy is its fashion. The looks, created by costume designer Mona May, have inspired more than two generations to don plaid yellow skirt suits, numerous fashion collections paying homage to the film’s stylish protagonist, and trends that are still having a moment almost 25 years later.
Of course, fashion is cyclical, so it’s no surprise that a quintessentially ‘90s trend like plaid — popularized by the grunge subculture’s thrift-shop aesthetic before turning mainstream — has made a comeback in recent years. Nor that slip dresses, a timeless wardrobe staple, never went out of style to begin with.
Still, when upon my most recent Clueless viewing last month, I spotted Cher’s tiny bag in a mall scene for the first time, I couldn’t help but note how on-trend it appeared. Looking barely big enough for a credit card — let alone a flip phone from that era — it may as well have been the crochet-savvy grandmother of one of Jacquemus’ popular Le Chiquito bags. As for the sheer trench that Cher layers over her Calvin Klein strapless dress, the one her father famously refers to as “underwear,” that was the same style I was waiting to come back in stock for most of last fall. I was totally buggin’!
After watching the movie with an eye for the trends that are still popular today, ahead, the six styles that prove that Cher was always a trendsetter.
Organza Tops
A master in layering, Cher gives her basic tanks and slip dresses a flair by throwing sheer button-downs and trenches over them. Organza blouses and trenches had a huge moment at the end of last year and, if we are to trust most recent collections, aren’t slowing down anytime soon.Photo: CBS via Getty Images.
Nasty Gal Sheer Heart Attack Balloon Organza Blouse, $, available at Nasty Gal
Cinq à Sept Erin Puff-Sleeve Organza Top, $, available at Saks Fifth Avenue
Dolls Kill Dark Legit Blurred Lines Organza Blouse, $, available at Dolls Kill
Zara PRINTED ORGANZA BLOUSE, $, available at Zara
Hair Accessories
Even before the pandemic reignited everyone’s love for hair accessories, scrunchies, padded headbands, and barrettes have made a strong comeback on their own. But it was Cher who unabashedly — some might even say iconically — paired a youthful version of the latter with a sexy red mini dress for her “date” with Christian.Photo: CBS via Getty Images.
RAINBOW UNICORN BIRTHDAY SURPRISE Betty Barrette, $, available at Rainbow Unicorn Birthday Surprise
BaubleBar Amber Hair Barrette Set, $, available at BaubleBar
Lele Sadoughi AQUA BOUCLE SLIM PADDED HEADBAND, $, available at Lele Sadoughi
DANNIJO Dionne Plaid Wool Headband, $, available at Saks Fifth Avenue
Tiny Bags
Cher’s teeny-tiny bag doesn’t get a lot of time on screen — and that’s a shame. Sage-colored and featuring a top handle that Cher casually holds it by, it’s a style that’s perfectly in line with her cutesy aesthetic and fashion’s frequent affinity for style over function. Despite the very many essays questioning the micro bag’s purpose in the last year, designers have sent down versions of the style as recently as the February runways — and we’re still fans.Photo: CBS via Getty Images.
Jacquemus Pink Check ‘Le Chiquito’ Clutch, $, available at SSENSE
By Far Mini Bag, $, available at Shopbop
Mlouye Mini Woven Bag – Cranberry, $, available at Mlouye
Boyy Brown Karl Charm Bag, $, available at SSENSE
Floral Babydoll Dresses
Created in the ‘40s, in response to wartime fabric shortages, the babydoll was originally intended as nightwear. But as we’ve seen most recently with the nightgown trend, a lot of sleepwear eventually becomes suitable (and fashionable) to wear outside the house. By the ‘90s, babydoll dresses shed their nighttime history and transformed into casual dresses, often in floral patterns as depicted on Cher. Two decades later, there are whole brands dedicated to the aesthetic.Photo: CBS via Getty Images.
Sleeper Brigitte Linen Mini Dress, $, available at Shopbop
Reformation Jo Dress Es, $, available at Reformation
Faithfull the Brand Ira Mini Dress, $, available at Neiman Marcus
BB Dakota Scattered Daisy Dress, $, available at Shopbop
Feather Sleeves
In what might be fashion’s most iconic film quote, Cher tells a robber who wants her feather-adorned Azzedine Alaia jacket, “You don’t understand this is an Alaia… It’s like a totally important designer.” But this isn’t the only important piece that features fluffy sleeves. In another scene, Cher showcases a knit cardigan with feather cuffs. Fast-forward to today, and you can find this sleeve detailing on pieces ranging from pajamas (Sleeper has made a name for themselves thanks to its popular styles) to button-downs.Photo: CBS via Getty Images.
ASOS CURVE Square neck cami with feather straps, $, available at ASOS
Sleeper Party Pajama Set with Feathers in Pink, $, available at Sleeper
Styland Long sleeve feather cuff silk shirt, $, available at Farfetch
Eliza J. Chiffon Capelet with Feather Trim, $, available at Nordstrom
Matching Sets
While Cher’s most iconic look is a plaid yellow suit, she wears other matching skirt sets throughout the film. With co-ords on the rise again, retro patterns like plaid, argyle, and houndstooth have particularly been trending, as well as two-pieces in knit materials.
Photo: CBS via Getty Images.
Maje Short jacquard cardigan, $, available at Maje
Eloquii Buffalo Plaid Sweater Column Skirt, $, available at Eloquii
Ronny Kobo Ashley Cable Knit Tube Skirt, $, available at Intermix
For Love & Lemons For Love & Lemons Cher Houndstooth Mini Skirt in Toffee, $, available at Revolve
Like what you see? How about some more R29 goodness, right here?
This Iconic Clueless Look Is Back
