As If! 15 Iconic Movies Like Clueless That Defined Teen Comedy And Fashion

Are you totally buggin' for a movie that captures the effortlessly witty dialogue, iconic fashion, and surprisingly good-hearted social commentary of *Clueless*? Released in 1995, Amy Heckerling’s masterpiece, starring Alicia Silverstone as the well-meaning but privileged Cher Horowitz, remains the gold standard for the teen comedy genre. It's a modern retelling of Jane Austen’s 1815 novel *Emma*, perfectly blending Beverly Hills opulence with a timeless story of self-improvement and matchmaking. As of today, December 10, 2025, the film’s influence is more visible than ever in new releases, proving that the high school hierarchy and the quest for a perfect outfit never go out of style.

To help you find your next cinematic obsession, we've compiled a definitive list of the best movies like *Clueless*, categorized by the specific elements they share—from sharp literary adaptations to modern, fashion-forward satires. Get ready to queue up the most iconic teen films of the last three decades.

The Witty Literary Adaptations: The Jane Austen Connection

One of the core brilliant elements of *Clueless* is its foundation in classic literature—specifically, Jane Austen's *Emma*. These films take a similar approach, proving that the drama of high school is just a modern update of timeless human folly.

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• 10 Things I Hate About You (1999): This is arguably the most direct spiritual successor to *Clueless*. It’s a clever modernization of William Shakespeare's *The Taming of the Shrew*. Set in a Seattle high school, it features sharp, quotable dialogue and breakout performances from Julia Stiles and the late Heath Ledger. The film brilliantly captures the angsty, intellectual side of teen life that Cher Horowitz would find "un-totes."
• Easy A (2010): A defining teen comedy of the 2010s, *Easy A* takes its premise from Nathaniel Hawthorne's *The Scarlet Letter*. Emma Stone stars as Olive Penderghast, a high schooler who embraces a scandalous reputation to help her social standing and financial situation. Like *Clueless*, it uses a classic text to satirize modern high school morality and features a quick-witted protagonist with a strong moral compass.
• Emma. (2020): For those who love the source material, this is a must-watch. Director Autumn de Wilde’s visually stunning adaptation of *Emma* is a vibrant, pastel-colored period piece that shares *Clueless*'s aesthetic focus on fashion and its central theme of a well-meaning matchmaker learning humility. Anya Taylor-Joy plays the titular role with a charm that echoes Cher’s own sweet cluelessness.

The Reigning Queens of High School Hierarchy: Satires and Social Commentary

If you loved the way *Clueless* dissected the social structure of a Beverly Hills high school, these films offer equally sharp and often darker takes on cliques, popularity, and the price of fitting in.

• Mean Girls (2004): Written by Tina Fey and starring Lindsay Lohan, *Mean Girls* is the other pillar of modern teen comedy. It moves the setting from Beverly Hills to suburban Illinois but maintains the focus on an outsider (Cady Heron) infiltrating a powerful clique (The Plastics). Its quotability and focus on the "burn book" and social rules make it an essential watch for any *Clueless* fan.
• Heathers (1988): A darker, more satirical precursor to *Clueless*, *Heathers* stars Winona Ryder and Christian Slater. It’s a black comedy that brutally satirizes the high school social structure, proving that the popular crowd can be truly menacing. While *Clueless* is warm, *Heathers* is icy, but both share a brilliant understanding of teenage power dynamics.
• The Duff (2015): This film, based on the novel by Kody Keplinger, offers a more modern look at high school labels. Mae Whitman plays Bianca, who discovers she is the "Designated Ugly Fat Friend" (DUFF) of her popular friends. It’s a funny, self-aware comedy that tackles the pressures of social media and labels, a theme Cher Horowitz would likely have to navigate today.

The Iconic Y2K & Modern Fashion-Forward Comedies

Fashion is a character in *Clueless*. Cher's plaid skirts, knee-high socks, and high-tech closet system are central to the film's identity. These movies carry the torch of visual style, where clothing is a key part of the character's journey or the film's aesthetic.

• Legally Blonde (2001): While not strictly a high school film, *Legally Blonde* is the spiritual college-era sequel to *Clueless*. Reese Witherspoon’s Elle Woods, a fashion-major sorority girl, is Cher Horowitz grown up. She uses her keen sense of style and good-hearted nature to navigate the elitist world of Harvard Law School, proving that being underestimated can be your greatest strength.
• Romy and Michele's High School Reunion (1997): Starring Mira Sorvino and Lisa Kudrow, this film is a vibrant celebration of female friendship and outlandish fashion. The two friends create elaborate lies and even more elaborate outfits for their high school reunion, capturing the same fun, bright aesthetic and deep bond between friends that defines the relationship between Cher and Dionne.
• She's All That (1999): This is the classic high school makeover movie. Freddie Prinze Jr. plays the popular jock who makes a bet to turn the "unpopular" artist (Rachael Leigh Cook) into the prom queen. It’s a classic 90s teen film that focuses heavily on the transformative power of a new look, a concept Cher Horowitz would wholeheartedly support.
• Bring It On (2000): A high-energy film that centers on high school competition and team drama, *Bring It On* is a snapshot of Y2K style and attitude. Starring Kirsten Dunst, it features snappy dialogue, a focus on cliques, and a vibrant, competitive spirit that makes it a perfect, energetic companion to *Clueless*.

Fresh and Current: The New Generation of Witty Teen Films (2019-2022)

In the last few years, a new wave of teen comedies has emerged, paying direct homage to the satirical wit and visual flair of *Clueless* and *Mean Girls*. These are the most current recommendations for a truly fresh watch.

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• Do Revenge (2022): This Netflix original is a Gen Z masterpiece that is often called a twisted blend of *Clueless* and Alfred Hitchcock's *Strangers on a Train*. Starring Camila Mendes and Maya Hawke, the film is a highly stylized, fashion-forward dark comedy about two high school girls who team up to take down their respective enemies. The colorful, preppy uniforms and the sharp, self-aware dialogue are direct nods to the Amy Heckerling classic.
• Booksmart (2019): Directed by Olivia Wilde, *Booksmart* is a critically acclaimed comedy that focuses on two overachieving high school seniors (Beanie Feldstein and Kaitlyn Dever) who realize they missed out on the fun and try to cram four years of partying into a single night. While less focused on fashion, it shares *Clueless*'s warmth, its celebration of female friendship, and its rapid-fire, witty script that instantly became a defining voice for a new generation.
• Can't Hardly Wait (1998): An essential entry for the ensemble cast energy. Featuring a large cast of recognizable 90s actors, this movie centers on a single high school graduation party where various social types—jocks, nerds, popular kids—converge for one messy, pivotal night. It captures the sheer fun and chaotic energy of the high school experience that is a necessary backdrop to Cher’s Beverly Hills world.
• Never Been Kissed (1999): Drew Barrymore stars as Josie Geller, a 25-year-old newspaper editor who goes undercover as a high school student. The film explores the universal desire to fit in and the painful reality of high school cliques. It’s a sweet, charming film that ultimately celebrates the good-hearted protagonist, much like the journey of Cher Horowitz.

Whether you're looking for iconic 90s nostalgia, a deep dive into high school social politics, or a modern movie with a killer wardrobe, these films offer the perfect blend of humor, heart, and high style that made *Clueless* an enduring cultural phenomenon. Grab your best friend and your most fashionable outfit—it's time for a teen movie marathon!