L'HISTOIRE: Lindsay Lohan’s Bustier and Ripped Jeans at the 2003 MTV VMAs

L'HISTOIRE explores fashion history moments you should know, from what actors wore on a red carpet to celebrities who made cameos on the runway. Some are unsung, and some are better known. Each is part of the fabric of today’s fashion world, be it barrier breakers or culture makers.

In the early 2000s, Lindsay Lohan was the ultimate it girl of Hollywood. From her breakout role in The Parent Trap to her performances in cult classics like Mean Girls, Freaky Friday, and Confessions of a Teenage Drama Queen, she cemented herself as a pop culture icon. On top of that, Lohan’s influence extended far beyond the screen. Yes, there was drama and scandal, but Lohan also led with trendsetting outfits, including on the red carpet, that made her a fashion inspiration for a generation of teenage girls. 

Freaky Friday was taking over pop culture in 2003, thanks to the then-new movie's star-studded cast, including Lohan, Jamie Lee Curtis, and 2000s heartthrob Chad Michael Murray. Lohan spent the summer basking in the spotlight during its late summer release, making red carpet rounds, including at the MTV Video Music Awards wearing a quintessentially Y2K look. She paired a crisp white button-down shirt layered under a black pinstriped bustier with suspender-like straps—a bold, on-trend choice. The 2000s red carpets were all about denim, so Lohan’s faded jeans fit right in. While we can’t see the rise, it’s safe to assume they were low-waisted, in true early-aughts fashion.

Completing the ensemble, the Freaky Friday star opted for pointy-toed heels and rimless ombré sunglasses, a staple accessory of Y2K fashion. She elevated the casual look a voluminous, layered hairstyle featuring soft curls and full bangs—another hallmark style of the time. With Freakier Friday—the highly anticipated sequel to Freaky Friday—set to release August 8, 2025, a new wave of Lohan’s iconic press tour looks is on the horizon.

To channel this Y2K-inspired look, opt for Miu Miu's retro-chic sunglasses and layer Dolce & Gabbana’s pinstriped corset under your favorite white button-down for a touch of preppy sophistication. Look into flare jeans, preferably faded, like True Religion's low-rise Joeys.