Hear me out: Confessions of a Teenage Drama Queen was one of the most iconic teen movies of the early aughts. The movie follows Lola, played by Lindsay Lohan, as she moves to the suburbs away from the hustle and bustle of New York City. Being a city girl, Lindsay’s character brought in a whole new attitude when it came to her style, ranging from a classic “I Heart NY” t-shirt paired with a fishnet long-sleeved shirt on top – because, duh! – to a mod-inspired minidress. Her character goes on to wear a variety of nostalgic looks like cargo pants, newsboy caps, and feathered coats that make us wish it was 2004 again.
Another thing we love? There were plenty of memorable songs, some sung by LiLo herself, such as “Drama Queen (That Girl),” which is currently being played on loop on TikTok. (I actually bought the CD back in the day and did’t regret it one bit.) It was pretty cool to see a young Megan Fox play the villain with style to boot. We’re talking matching leather jackets with her posse, along with Tiffany & Co. heart chainlink necklaces. Ahead, we’re counting down 15 style moments from the movie we still dream about from time to time.
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Was there anything more badass in the early aughts than a graphic-print tee paired with low-rise pants? I think not.
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I don’t know where to start with this nostalgic outfit: the cargo pants or the trucker hat?
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Remember wanting Lindsay Lohan‘s Coca-Cola bottle top necklace? I certainly do.
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What could show off your teenage angst more than an “I Heart NY” tee with a fishnet shirt on top?
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Now this mod-inspired baby blue dress was a *lewk* if I’ve ever seen one.
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Wearing a sheer feathered white coat with knee-high boots to school? Why not.
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It doesn’t get more boho than styling a flowy top with a scarf tied around your head.
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That top! Those pants! Those ruffles! Oh-my!
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We’re still not over Lindsay’s ruby-red sequin dress and Alison’s brooch.
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Of course, Lindsay’s messenger bag was a big part of her wardrobe in the movie.
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There were plenty of amazing hat moments in the movie. Case in point? This suede newspaper boy one.
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You can’t go wrong with a leather jacket and a Tiffany & Co. necklace.
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This fringed jacket really embodied Lindsay’s free spirit, don’t you think?
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I know we’re supposed to dislike Megan Fox in this movie, but I couldn’t help but love her all-black look paired with a silver chain belt.
Everett Collection / Buena Vista Pictures/Courtesy Everett Collection
Alison’s henley polo is actually back in style now!
