The 11 Sassiest Looks From Early 2000s Films

Once upon a time, the thought of compiling a list of the best, sassiest looks from early 2000s films would have made me cringe. A decade arguably frowned upon ever since its occurrence, the years between 2000 and 2005 in particular have been criminally overlooked when it comes to style — until now. Finally, the sassy clothes and completely over-the-top tacky outfits from my late childhood years are grabbing the attention they deserve. The early '00s is the new late '90s, bare midriffs, tinted sunglasses, florescent fake fur, and all.

What better way to remember the decade, and research some much-needed outfit inspiration, than by taking a look back through the era's best films? And by best films, I don’t mean critically-acclaimed. I’m talking about the most influential movies of the first years of the ‘00s in terms of not number of awards won, but best looks served.

It’s high time we stopped cringing at our old wardrobes. Here, I’m taking a look back at the coats, shoes, bags, and dresses that aren’t just so-bad-it’s-good. When you flash-forward 10 years, I'm personally still dying to have them in my wardrobe. Below are 11 of the sassiest ensembles and most killer costumes from early millennium cinema.

1. Elle Woods In Legally Blonde

The character who single-handedly taught me that beauty does not equate to compromising your brains, Elle Woods' juggling of a Harvard Law degree while serving looks that remain second-to-none has meant that her character has gone down in history as a modern-day feminist icon.

2. Penny Lane In Almost Famous

Almost Famous' interpretation of '70s groupie style via the early '00s totally echoed what Gucci is doing on the runway right now, with current campaign girl and feminist photographer Petra Collins giving Kate Hudson (aka Penny Lane) a run for her money in 2016.

3. Scarlett Johansson's Pink Wig In Lost In Translation

Sofia Coppola's melancholic love letter to Tokyo featured many eye candy-worthy moments. However, my favorite costume from the film would have to be her now-iconic pastel pink wig.

4. The School Uniforms In The Princess Diaries

Hear me out on this one. Those Peter Pan collars were totally cute. Plus, Mia's best friend Heather's choker and scrunchie combo was totally amazing.

5. Every Single Outfit In Moulin Rouge!

From OTT headdresses to an uncountable number of corsets and dripping diamonds, king of opulence Baz Luhrmann's Moulin Rouge! epitomized the era of early '00s eleganza.

6. Margot Tenenbaum's Fur In The Royal Tenenbaums

Margot Tenenbaum's poker-straight hair, heavy eyeliner, and that perfectly-placed hair clip cemented her character as a sad-girl icon.

7. The Boiler Suits In Charlie's Angels

Now, this entry may be a remake of the '70s classic. But that doesn't mean there aren't sassy early '00s gems to be found throughout the film. My personal favorite is still Drew Barrymore's take on a car mechanic's uniform, completed with a cherry red lip and bright blue lenses.

8. The Pageant Costumes In Miss Congeniality

All patriotism aside, these dresses held all the makings of an early '00s masterpiece: Off-the-shoulder sleeves, silky satin that snagged, and a thigh-high slip that ran all the way up to the hip.

9. Enid Coleslaw's Cat Mask In Ghost World

Snapped up at a sex shop, Enid Coleslaw's mask, glasses, and Peter Pan collar combo paved the way for every Tumblr-loving-weird-girl for years to come.

10. Britney Spears' Many Midriff-Baring Blouses In Crossroads

Many have already made the case for embracing our midriffs as enthusiastically as pop stars did in the early '00s, but Britney Spears' tale of a cross-country trip featuring multiple exposed bellybuttons only makes me want to cut all my T-shirts to half their length that little bit more.

11. Lizzie McGuire's Twinning Moment In The Lizzie McGuire Movie

Taking down an egotistical Italian pop star with your body double/long lost twin in matching pearlized lime and lilac biker jackets is definitely a more productive way to spend your summer holiday than I ever managed.

Whether you're into S&M-like sex masks, opulent showgirl costuming, or school girl chic, these early '00s icons will surely prove that it's not so ridiculous to start incorporating sassy early millennium style back into our wardrobes. That said, I'm not sure I'm quite ready to rock more than one trend at once just yet.

Images: Metro-Goldwyn-Mayer (1); Dreamworks Pictures (1); Focus Features (1); Walt Disney Pictures (2); 20th Century Fox (1); Buena Vista Pictures (1); Columbia Pictures (1); Warner Bros. Pictures (1); United Artists (1); Paramount Pictures (1)