Can we all just take a minute to appreciate how many cultural *moments* Lindsay Lohan gave us in the early aughts? Her movies are classics to all of us that grew up watching Disney Channel not to mention her highly covetable wardrobe in those films. With certain 2000s trends creeping into modern fashion (for better or worse), let’s reminisce about those years with one of the most fashionable celebrities of the time.
No one did it like LiLo. She was consistently stylish in most all of her films and those movies are often referenced and have proven their staying power (You go, Glen Coco!). This trip down memory lane will look at some of Lohan’s most iconic looks in her most legendary movies: Freaky Friday, Confessions of a Teenage Drama Queen, and Mean Girls. Get ready for some behind-the-scenes details about the costume design and general Lohan fangirling.
Could you, like, chill for a sec? Freaky Friday had it all, G-rated punk rock, teenage angst, a sassy Jamie Lee Curtis, and edgy ensembles by Genevieve Tyrrell. Even though Lohan was a household name by this time, this was only her second film released in theaters!
This look wasn’t actually worn in the film, but this promotional photo really represents what Anna’s all about. The punk aesthetic, heavy eye makeup, and customized denim jacket tell us she’s not your average girl next door. She’s got spunk, she’s a rebel, and she’s got the scowl and attitude to match. Avril Lavigne who?
The Guitar Tee
Anna’s style was the epitome of early aughts punk rock. Apparently, her character was supposed to be full-on goth, but was rewritten after Lohan showed up to her audition clad in Abercrombie & Fitch.
Lohan shredded the guitar, jumped up and down, and generally rocked out to “Ultimate” in this skin-tight ankle-length dress. What a moment.
Confessions of a Teenage Drama Queen
In the words of Miss Baggoli, costumes are sacred. And these costumes elevated LiLo to the status of fashion icon. She pulls off just about every style imaginable in this one film. The wardrobe is just as extravagant and colorful as Lola’s dramatic nature and we have costume designer David C. Robinson to thank for that!
I Love New York
It’s hard to pin down Lola’s style; it’s part punk, part bohemian with a hint of retro, but all fabulous. This long-sleeve fishnet top over the I Love New York shirt is such an edgy take on the classic tee. Lola accessorizes with her signature Coke bottle necklace.
Retro Patchwork Jacket
Newsboy hats were so big in the early 2000s. She pairs this one with a retro patchwork jacket for a look that would still be stylish today!
Hippie Head Wrap
I’m getting late ‘60s early ‘70s hippie, free love vibes from this head wrap and embellishments. Of course, her Coke bottle necklace completes the retro look.
Little Red Dress
Probably the most iconic outfit from the movie that survived a thunderstorm and an evening in a police station. I totally get why she risked it all to wear this dress, it’s flashy and anyone who lays eyes on it will give you their undivided attention.
When I tell you LiLo served us looks in the early 2000s, this is what I’m talking about. A look. A mood. A moment! Lola dons this colorful feathery number for her big finale number “Drama Queen.” It’s so over-the-top and perfectly encapsulates her flair for the dramatic.
Easily Lohan’s most memorable and quotable film. According to costume designer Mary Jane Fort in a video breakdown of Mean Girls looks by Vanity Fair, the outfits for Cady and the Plastics was inspired by a candy store—everything colorful, shiny, and sweet. We can definitely tell; the looks were so fetch!
Cady looked tragic in this thrifted bride of Frankenstein getup. Fort wanted her to look as different as possible from everyone else to signify her outsider status before her transformation into a Plastic.
Trash Can Chic
This look marks Cady’s introduction to the school as a full-fledged Plastic. Fort added the frilly trim, so it would puff out like tissue paper when Cady falls into the trash can. Fun fact: this is Fort’s favorite costume.
Jingle Bell Rock Costume
By this time Cady is officially one of The Plastics and has graduated to become Regina’s “#2.” A subtle nod to Cady’s follower mentality is her bare midriff, which copies Regina’s. The miniskirts were made of plastic, of course.
Pink Stripe Dress
Lohan wanted to add something more to this dress, so she and Fort decided to add the hot pink bra as a fashion statement. Let’s be honest, we all wanted to copy this style when we were younger because Lindsay made it look so dang cute.
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