Lindsay Lohan’s 10 Most Iconic Fashion-World Exploits
Most celebrities’ impact on the fashion industry could be wrapped up with a gallery of their best red carpet looks, but Lindsay Lohan is no ordinary celebrity. She’s an era-defining force of nature whose impact on all aspects of pop culture could be studied for decades—but might simply be summed up with: “You really had to be there.” In between her string of beloved young adult classics (Mean Girls, The Parent Trap, et al.), her constant tabloids exploits, and a few court dates, she was omnipresent on the fashion circuit. A highly sought-after front-row guest, Lohan inspired one of the most controversial Chanel bags of all time. For a very brief period, she even had a design role at a historic French fashion house.
Today marks Lohan’s 40th birthday, and her wildest days are now behind her. She’s a happily married mother of one with a revived career. Freakier Friday was a solid financial hit at last summer’s box office, and she’s recently been spotted filming the buzzy Hulu mini-series Count My Lies with Shailene Woodley and Kit Harington throughout New York.
It turns out, you can really heal, mature, and change for the better, but Lohan’s exploits in the fashion industry remain timeless. Here, her 10 most memorable moments.
Her Very First Fashion Show
It’s 2003. Lohan is just 17, and the release of Freaky Friday is still a few months away, but she made her very first fashion week appearance at Nicole Miller’s fall 2003 show at the tents in Bryant Park during New York Fashion Week. Clearly, it would not be her last.
It Bag Queen
In the 2000s, a bag wasn’t really an It bag until it was seen in the tabloids on the arms of numerous starlets. Lohan was one of the most prolific It bag owners of the time, often spotted with classics like the Balenciaga Le City bag, Chloé Paddington, Chanel 2.55, and an occasional Birkin.
Her Karl Lagerfeld Muse Era
During his life, Karl Lagerfeld was arguably the most powerful man in fashion, but he wasn’t a gatekeeper. The late Chanel and Fendi creative director was often the first to invite tabloid sensations, underground wunderkins, and promising youth culture standouts into high fashion’s fold. Lohan was no exception. Throughout the years, Lagerfeld hosted Lohan at numerous parties, a few Chanel shows, and even brought her as his date to the 2006 CFDA Awards.
...and The Resulting Anklet bag
During her various legal troubles, Lohan was famously forced to wear ankle monitors on three separate occasions, and once took to Twitter to ask Chanel for some stickers to add just a little bit of chicness to the device. Lagerfeld did one better. For Chanel’s spring 2008 collection, he shrunk down the brand’s 2.55 bag to an ankle-appropriate size.
Her W Cover with Meryl Streep
Obviously, we’re biased, but we just can’t ignore the objective truth that Linday Lohan’s joint cover with Meryl Streep (the pair were co-starring in the Robert Altman movie A Prairie Home Companion at the time) was absolutely major.
Her Ugly Betty Arch
Trading in on her numerous scandals and fashion-favorite image, Lohan had a highly publicized narrative arch on the third season of Ugly Betty, playing one of the title character’s old bullies.
The Fornarina Commercial
In 2009, Lohan served as the face of the Italian youth label Fornarina. The very European ad was clearly meant to cut through any language barriers, but still found its way back to Americans thanks to YouTube. Obviously, the spoken-word song that serves as the soundtrack remains a cult classic. Good luck getting “Bang! Wink! Smash! Fornarina!” out of your head.
Her Stint at Ungaro
By 2009, the world of high fashion had realized the growing power of celebrity, they just didn’t know how to fully optimize it. Perhaps you can’t blame the powers that be at Ungaro for trying to find a solution. They dismissed previous designer Esteban Cortázar, signed Lohan on as an “artistic advisor” and hired Estrella Archs to help her vision come to life. This arrangement lasted exactly one season: spring 2009. Reactions were...not good. Lohan quickly departed, but Archs continued on for a few seasons.
Our only question: in this era of celebrities engaging in a red carpet arms race of archive pulls, why hasn’t someone tried to find one of these pieces and make it work on the step and repeat?
Her Law Roach-assisted Red Carpet Renaissance
After marrying financier Bader Shammas in 2022, Lohan reemerged into the world as a new woman. That required a new look. She enlisted super-stylist Law Roach to help handle her outfit to promote the Netflix film Falling For Christmas. His work included sourcing this vintage Valentino gown for the film’s premiere.
Her Demna Muse Moment
Lindsay Lohan’s eventual link-up with Demna always seemed like a question of “when,” not “if.” The Georgia-born designer often plumbs the Y2K starlet aesthetic, which Lohan helped exemplify. She first showed up in on of Demna’s front rows for his spring 2025 collection for Balenciaga, and their relationship seems to have continued now that Demna has moved to Gucci. She was also front row for the Italian brand’s recent cruise collection show in Times Square.
