While not primarily focused on high fashion, A Walk to Remember captures a specific, more subdued slice of early 2000s style through its protagonist, Jamie Sullivan (Mandy Moore). Her wardrobe reflects her serious, religious character: modest oversized sweaters, long denim skirts, simple turtlenecks, and practical footwear. This contrasts sharply with the more trend-driven popular kids at school. Costume designer Doug Hall used Jamie's simple, unchanging style to emphasize her inner substance over outward appearances. It represents the girl-next-door, slightly preppy but conservative look that existed alongside the flashier Y2K trends popularised by pop stars. The fashion here serves the heartfelt story rather than making bold statements, offering a quieter, but still distinct, look back at the era.

Never Been Kissed gives us a double dose of fashion: awkward high school flashbacks and late 90s professional chic. Drew Barrymore as Josie Geller navigating high school undercover provides plenty of memorable looks. Who could forget her disastrous white feathered boa ensemble for her ill-fated prom attempt? Or her attempts to fit in with the cool kids in slightly off-trend outfits? Contrasted with her job as a copy editor, where she dons more sophisticated (for the time) sheath dresses and cardigans, the film uses fashion to chart Josie's journey from 'Josie Grossie' to confident woman. It's charming, relatable, and features some truly unforgettable (if sometimes cringey) style moments, especially that prom outfit which costume designer Mona May clearly had fun creating.

The 2003 remake of Freaky Friday used fashion brilliantly to highlight the body-swapping chaos between mother Tess (Jamie Lee Curtis) and daughter Anna (Lindsay Lohan). Anna's wardrobe is pure early 2000s punk-rock teen: baggy cargo pants, band tees (like The Hives), studded belts, layered tanks, and heavy eyeliner. Tess, meanwhile, embodies sophisticated therapist chic with tailored pantsuits and blouses. When they switch, the visual comedy of seeing Curtis rock Lohan's grungy attire and Lohan navigate Curtis's more conservative clothes is priceless. Costume designer Genevieve Tyrrell used the distinct styles to emphasize their generational clash and eventual understanding. Anna's band's performance look is also a notable snapshot of the era's pop-punk aesthetic.

Hey now, hey now! This is what dreams (and early 2000s fashion) are made of! The Lizzie McGuire Movie took the beloved Disney Channel character's quirky style and gave it a Roman holiday glow-up. Hilary Duff served peak Y2K tween/teen looks: colourful capris, layered tops, platform sandals, crimped hair, newsboy caps, and butterfly clips galore. The fantasy sequence where Lizzie transforms into Italian pop star Isabella Parigi dialled up the fashion even more, featuring that unforgettable metallic green inflatable igloo dress. It's a pure, concentrated dose of the era's optimistic and often eccentric pop-influenced style, perfectly capturing the transition from TV show favourite to movie star. Sing to me, Paolo!

This quintessential 1999 teen rom-com hinges on a makeover, making fashion a central plot point. Laney Boggs' (Rachael Leigh Cook) transformation from 'art geek' in paint-splattered overalls and glasses to conventionally stunning prom queen candidate in that red dress is the film's most memorable fashion moment. Designed by Denise Wingate (again!), the movie showcases classic late 90s trends beyond the makeover: Zack Siler's (Freddie Prinze Jr.) casual button-downs and khakis, Taylor Vaughan's popular-girl mini skirts and crop tops, and the general aesthetic of high school hierarchy expressed through clothes. While perhaps not as boundary-pushing as others on this list, its depiction of the transformative power of a new outfit (and removing glasses) cemented its place in teen movie fashion history.

Brr, it's cold in here! There must be some Toros in the atmosphere! Bring It On brought competitive cheerleading—and its distinct fashion—into the spotlight. Beyond the iconic Rancho Carne Toros and East Compton Clovers uniforms, which became instantly recognizable, the film showcased casual early 2000s style. Think logo tees, track pants, halter tops, bandanas worn as headbands, and plenty of athletic wear transitioning into everyday looks. Kirsten Dunst as Torrance Shipman and Gabrielle Union as Isis led their squads not just in routines but in Y2K style. Costume designer Mary Jane Fort (who also did Mean Girls) captured the spirit of high school athletes at the turn of the millennium. It's a vibrant display of spirit fingers and spirited fashion.

Cruel Intentions brought a dark, sophisticated, and overtly sensual edge to late 90s teen fashion. Set amongst the privileged youth of Manhattan's Upper East Side, the clothing reflected wealth and calculated allure. Kathryn Merteuil (Sarah Michelle Gellar) wielded her wardrobe like a weapon, favouring sharp tailoring, corset tops, sleek black ensembles, and that unforgettable lingerie-as-outerwear moment. Annette Hargrove (Reese Witherspoon) provided a contrast with her more classic, subtly preppy, 'good girl' style. Sebastian Valmont (Ryan Phillippe) perfected the brooding, rich bad boy look. Costume designer Denise Wingate crafted looks that felt expensive, mature, and dangerously chic, perfectly complementing the film's manipulative games and dark themes. It's 90s prep school style with a venomous bite.

A cornerstone of late 90s teen cinema, 10 Things I Hate About You offers a fantastic snapshot of the era's contrasting styles. You have Kat Stratford (Julia Stiles), the fiercely independent, alt-rock loving feminist whose wardrobe consists of cargo pants, camo print, simple tanks, and subtly grunge vibes. Then there's her younger sister Bianca (Larisa Oleynik), embodying the more mainstream femininity of the time with her crop tops (especially that iconic floral one!), pastel cardigans, and delicate accessories. Costume designer Kim Tillman nailed the distinct personalities through their clothes. Even the supporting cast, from Chastity Church's preppy looks to Mandella's Shakespearean obsession, contributes to the rich fashion tapestry. And let's not forget those prom dresses – Kat's simple navy slip vs. Bianca's pink tulle confection.

This movie is peak Y2K maximalism and deserves way more credit for its incredibly fun and fearless fashion. Josie and the Pussycats took the burgeoning trends of the new millennium – low-rise everything, animal print, glitter, bandanas, visible thongs, baby tees, frosted lip gloss – and dialled them up to eleven. Costume designer Leesa Evans created distinct but coordinated looks for Josie (Rachael Leigh Cook), Val (Rosario Dawson), and Melody (Tara Reid) that perfectly embodied their pop-punk band persona. The sheer amount of leopard print alone is staggering! It's a satirical take on consumerism, but the fashion itself is a genuine, joyous explosion of early 2000s style, capturing the playful, slightly chaotic energy of the era's pop culture.

Before 'dark academia' was a hashtag, there was The Craft. This 1996 cult classic brought witchy, goth aesthetics into the high school mainstream. Nancy, Rochelle, Sarah, and Bonnie served up peak mid-90s alternative style: pleated mini-skirts paired with combat boots, layered slip dresses over baby tees, crucifixes and chokers galore, dark lipstick, and lots of black. Costume designer Deborah Everton expertly used clothing to differentiate the four witches' personalities while creating a cohesive coven look that felt both rebellious and cool. Their outfits were a far cry from the preppy styles dominating other teen movies of the time, offering a darker, edgier inspiration that still resonates within alternative fashion circles today. We are the weirdos, mister, and we have the best outfits.

Whoever said orange was the new pink was seriously disturbed! Elle Woods, portrayed iconically by Reese Witherspoon, weaponized fashion, proving that a passion for pink and Prada doesn't negate intelligence. Legally Blonde is a celebration of unapologetic femininity, channelled through Elle's overwhelmingly pink, often fluffy, and always perfectly accessorized wardrobe. Costume designer Sophie de Rakoff used Elle's clothes to chart her journey from sunny California sorority girl to determined Harvard Law student, never sacrificing her personal style. Think head-to-toe monochromatic looks, tiny sunglasses, embellished tops, and let's not forget Bruiser Woods' coordinating outfits! Elle challenged the stuffy, dark palette of Harvard with her sunny disposition and equally bright clothes, making a powerful statement about staying true to yourself. What, like it's hard?

Get in loser, we're going shopping! Mean Girls defined the look of the early 2000s Plastics with fetch precision. Regina George, Gretchen Wieners, and Karen Smith served up a masterclass in Y2K trends: Juicy Couture tracksuits (a cultural reset!), mini skirts paired with tight tops, designer bags swinging from their arms, and, of course, adhering to the strict 'On Wednesdays, we wear pink' rule. Costume designer Mary Jane Fort perfectly captured the hierarchy of high school through clothing, from the Plastics' calculated chic to Janis Ian's artistic grunge and Cady Heron's journey from khaki-clad newbie to Plastic wannabe. The film is a time capsule of flip phones, low-rise jeans, and slogan tees ('Fetch' may not have happened, but the fashion certainly did). It's endlessly quotable and just as visually iconic.

As if! Could any other film possibly top this list? Clueless isn't just a movie; it's a mid-90s fashion bible disguised as a brilliant Jane Austen adaptation. Cher Horowitz (Alicia Silverstone) and her bestie Dionne (Stacey Dash) ruled Bronson Alcott High with their coordinated plaid skirt suits, sheer tops layered over tanks, knee-high socks, and an endless parade of fuzzy accessories and tiny backpacks. Costume designer Mona May crafted over 60 looks for Cher alone, creating a high-fashion fantasy that still inspires runway collections and Halloween costumes decades later.

Remember Cher's revolutionary digital closet? That pre-dated actual styling apps by years! The film seamlessly blended high-end designers like Calvin Klein (that dress!) and Azzedine Alaïa ('An A-what-a?') with mall staples, making aspirational style feel somewhat accessible. It perfectly captured the optimistic, slightly preppy, yet playful fashion landscape of the era. Totally essential viewing for any fashion devotee.