2000s Movies with the Best Fashion, Ranked

The 2000s had a lot to offer. Great music, iconic pop culture references and so many quintessential fashion moments. Even if you’re not a fashion lover or someone who pays attention to trends, you can likely spot a Y2K look from a mile away.

2000s fashion was big on low-rise jeans, Von Dutch trucker hats, rugby shirts, Juicy Couture tracksuits, graphic tees, cargo pants, dresses over jeans, halter tops — the list goes on. Brands like Baby Phat, Ed Hardy and True Religion were the holy grail and people often looked to style icons of the time like Paris Hilton, Britney Spears, Beyoncé, Sarah Jessica Parker, and Christina Aguilera for fashion inspiration.

A lot of naughties-style inspo also came from the big movies during the time. Seeing the looks actresses like Lindsay Lohan, Mary Kate and Ashley Olsen, and Hilary Duff wore on the big screen inspired new trends among audience members as they aspired to recreate the looks from their favorite movies. In fashion, trends come and go. Much of what was considered “cool” in the 2000s is seen as cringy by a lot of people today. However, a lot of those Y2K trends are starting to make their way back into the limelight today.

If you’re looking to reignite the naughties in your own closet, here are seven movies from the 2000s with the best fashion.

7 The Devil Wears Prada (2006)

This 2006 dramedy based on Lauren Weisberger’s novel of the same name, is about Andy Sachs (Anne Hathaway), an eager college graduate who gets a job as the new assistant to the powerful fashion magazine editor Miranda Priestly (Meryl Streep), with Emily Blunt and Stanley Tucci in key supporting roles.

With the movie being based in the fashion world, The Devil Wears Prada is full of chic looks often seen on the streets of New York City in the early 2000s. Think knee-high leather boots, stacking patterns, chunky necklaces, layers, statement belts, and tweed caps. The Devil Wears Prada blends both elegant street wear with high-fashion, office-ready styles, inspiring fashionistas everywhere to want to work for a magazine like Andy.

6 Bring It On (2000)

This 2000 movie is all about a high school cheerleading team preparing for a national competition, starring Kirsten Dunst, Gabrielle Union, Jesse Bradford, and Eliza Dushku. Trends obviously ebb and flow over time, but with Y2K on the rise, Bring It On is a treasure trove of outfit inspiration.

A lot of the fashion in Bring It On is very athleisure-focused — it’s a cheerleading movie — but athleisure is very “in” right now. If you take one look on the streets anywhere, you’re guaranteed to see biker shorts, sports bras as tops, crop tops and monochromatic athleisure fits. Bring It On also featured iconic high ponytails, frosted eyeshadow, cropped cardigans and bandanas — all of which still look great today.

Related: Funny Face: A Fashion Masterpiece Long Before Devil Wears Prada

5 13 Going on 30 (2004)

2004’s 13 Going on 30 is such a fun, feel-good movie. It’s about a 13-year-old girl in 1986 who, after being humiliated by her classmates during her birthday party, makes a wish that she was 30-years-old. When she wakes up, her wish comes true, and she’s 30-years-old in 2003, with no idea how she got there.

The movie is cute, funny and overall just a blast to watch, and Jennifer Garner’s performance is perfect. However, one of the best parts of 13 Going on 30 is its fashion. Everyone knows the signature colorful striped Versace babydoll dress Garner wears in the memorable dance scene, complete with spikey buns, a butterfly necklace, and strappy heels. The dress alone makes 13 Going on 30 instantly identifiable. The movie also featured tons of baguette bags — which are very trendy today.

4 Legally Blonde (2001)

Legally Blonde‘s Elle Woods (Reese Witherspoon) has been a fashion icon since the movie premiered in 2001. Sorority girl turned lawyer Elle Woods is constantly serving looks — most often in varying shades of pink, with a little sparkle here and there.

The outfits in Legally Blonde just scream 2000s and feel so much larger than life. From Elle’s pink two-piece and matching sunglasses she wears when she arrives at Harvard, her sparkly bikini top and fluffy pink coat, to her various pink halter tops and the infamous pink, collared dress with the sparkly sash she wears during her court scene. Simply put, Elle Woods made pink cool.

3 Freaky Friday (2003)

2003’s Freaky Friday is the ultimate body-swap movie. It stars Lindsay Lohan as Anna and Jamie Lee Curtis as Tess, a mother-daughter pair whose bodies are switched thanks to a mysterious, magical fortune cookie at a Chinese restaurant. In terms of fashion, Freaky Friday really shines a spotlight on the mall punk aesthetic of the early 2000s.

Lohan sports chunky highlights, studded belts, baggy cargo pants, and converse. It’s very Avril Lavigne-esque. There’s also plenty of plaid, chained pants, dark eyeliner, crop tops, patched denim jackets, and grungy layers that have had a hold on the punk scene for decades — long before Freaky Friday and still today.

Related: Bridgerton’s Lasting Impact on Today’s Fashion

2 The Lizzie McGuire Movie (2003)

2003’s The Lizzie McGuire Movie is a masterclass in fashion and can honestly still be referenced for style inspiration today. The movie stars Hilary Duff as Lizzie McGuire as she takes her high school graduation trip to Rome. The movie also serves as the finale to the Disney Channel series of the same name.

Much of Lizzie McGuire’s outfits were often quirky and a little mismatched and out of the ordinary, but they were worn in such a way that was still refined and inspired countless people’s looks. The Lizzie McGuire Movie is such a fashion plate, there are almost too many stand-out looks to mention. From Lizzie’s ruffled button-downs, to her butterfly clips and baker boy caps to the iconic ensemble worn in the “What Dreams Are Made Of” performance — it’s high fashion all around.

1 Confessions of a Teenage Drama Queen (2004)

Confessions of a Teenage Drama Queen is another hit teen movie from the early 2000s starring Lindsay Lohan in the lead. It’s about Lola (Lohan) an aspiring actress whose plans hit a road block when her family moves from NYC to New Jersey. Once at her new school, Lola sets off on a mission to become the most popular girl in school. While the movie itself can come off as a little cheap and lacking, we’re really just here for the fashion.

Confessions of a Teenage Drama Queen manages to blend all the best elements of Y2K fashion seen in other hit movies into one feature. One of the most iconic is Lola’s fishnet top over her “I heart NY” tee, complete with low rise jeans and a bottle cap necklace. The movie also showcases patchwork jackets, the 2000s signature baker boy cap, monogrammed bags, hoop earrings, trucker hats, and signature designer items from big names like Tiffany and Dior — all of which are hot commodities at any popular retailer today.