Ugh, As If

Clueless redefined high school fashion, turning knee-high socks and coordinated plaid into a lasting style legacy.

There are films where fashion is a backdrop, and then there are films like Clueless, where fashion is the story. Released in 1995 and directed by Amy Heckerling, Clueless is a loose adaptation of Jane Austen’s Emma, filtered through the kaleidoscope of Beverly Hills prep schools and Valley Girl slang. But what’s elevated it from teen rom com to cultural icon is Mona May’s costume design. Outfits that weren’t just ahead of their time, but continue to influence style decades later.

She gave us Cher Horowitz, the teen queen of matching plaid and high standards. From the moment she appears in that yellow tartan blazer and skirt set complete with knee high socks and a white collar, we know exactly who she is: polished, sunny, confident, and in control. It’s fashion that announces her status, her wealth, and her obsession with perfection. She literally uses a computer program to choose her outfits (before that was normal), and yet nothing ever feels sterile or overly serious. Cher is curating her life like it’s a lookbook.

What makes the Clueless wardrobe so memorable is how it plays with aspiration. These are high schoolers, yes, but they dress like they’re on the cover of a fashion mag. There’s something tongue in cheek about the hyper stylized prep: blazers, mini skirts, sheer blouses, fluffy pens, and platform Mary Janes. It’s the costume designer’s understanding that teenage girls often dress not for comfort, but for effect. To project maturity, to experiment with identity, to feel powerful, to be seen.

And Cher’s never boring. Her looks are coordinated within an inch of their lives, but never repetitive. Plaid is reimagined in various colors. She layers with tiny cardigans and sheer tops, mixing textures like a pro. There’s an obsessive attention to detail, something that could come off as superficial, but in Clueless, reads as a form of care. Cher dresses for every moment of her life like it’s worth showing up for, and there’s something quietly empowering about that.

Then there’s Dionne, Cher’s equally stylish best friend, whose fashion sense is louder and more experimental. Her looks are bold, sometimes even costume-y, with hats, patterns, and vinyl textures that scream individuality. She’s not Cher’s sidekick, she’s got her own thing going, and Mona May gives her a wardrobe that matches her energy. If Cher’s about sleek coordination, Dionne’s about statement pieces. Together, their looks form a visual language of friendship, competition, and shared confidence.

When Tai enters the scene, the costume shifts are used to chart her journey. Her early looks are baggy, messy, casual. She’s not trying to impress anyone. But as she gets Cher’s makeover treatment, her clothes become tighter, more colorful, and more styled. It’s transformation via tube top. But interestingly, as Tai gains confidence, the film resists turning her into a Cher clone. The clothes evolve, but they never erase her essence. It’s a smart costume arc, showing us that while fashion can be transformative, it doesn’t have to be homogenizing.

What’s most enduring about Clueless‘s costuming is that it’s a time capsule that doesn’t feel dusty. Even now, you’ll see its influence in runway collections, TikTok trends, and Pinterest boards. It’s not just the plaid or the platforms, it’s the spirit of carefully curated fun. These clothes aren’t about looking sexy or grown up; they’re about playing dress up with intention. They’re about expressing mood, status, and imagination. Every outfit is a choice, and Clueless made those choices with precision.

Mona May wasn’t just designing for the trends of the moment, she was creating style language. That’s why, nearly 30 years later, Cher’s yellow plaid suit still feels fresh, still makes Halloween costumes, still inspires capsule wardrobes. Clueless didn’t just mirror the 90s, it helped shape them.

Every outfit in Clueless is deliberate. Fashion becomes a statement of identity, confidence, self protection, and self admiration. In a world quick to dismiss teen girls, the film insists on their complexity. The clothes say what others refuse to hear.