Lindsay Lohan's Most Inappropriate Outfits Ever

With 2000s nostalgia making a comeback, actor and musician Lindsay Lohan has ridden this wave back into the spotlight. Thanks to a multi-film deal with Netflix, the Lohanaissance is fully underway. When "Irish Wish" and "Our Little Secret" hit the streaming service's platform in 2024, it was the first indication that Lohan was ready to waltz back into our hearts and minds. As the media frenzy for the "Freaky Friday" sequel started ramping up, it also gave Lohan a chance to show off one of her more unique talents: wowing on the red carpet. For better or for worse.

Not every outfit Lohan has worn has been a winner — the 2000s and 2010s were not kind to the fashionistas of the world. As Lohan transformed from a child star to hot mess to responsible adult, so too has her sense of fashion followed a chaotic trajectory. From scandalous courtroom dresses to forgetting to put on pants, we've rounded up some of Lohan's most inappropriate outfits of all time.

Riding the high of success that starring in "Freaky Friday" brought her, Lindsay Lohan was having an excellent 2003 — except for the fashion she sported for much of it. Seen here on the red carpet for the MTV Music Video Awards, Lindsay appears to be channeling her inner "wine mom." With those tinted sunglasses and exaggerated bangs, Lindsay looks more like her mother (and fellow lawbreaker) Dina Lohan than a teenager. Most egregious might be the distressed denim — an unfortunate staple of 2000s fashion. The flared jeans, of course, completely cover Lindsay's shoes, another troubling trend from the era. Although, most of this would be forgivable if Lindsay weren't on the red carpet.

Attending award shows is both a perk and a demand of the job of being famous. Here, Lindsay doesn't quite nail the appropriate dress code. The jeans are too dressed-down, and the tiny vest over the giant white shirt is distracting, to say the least. However, these fashion faux-pas didn't hold Lindsay back. After learning to play guitar for "Freaky Friday," she was able to launch a reasonable music career. Which makes it easy to chalk this look up to "misguided rock star."

2009 was a tumultuous year for Lindsay Lohan. With her on-again, off-again romance with Samantha Ronson, Lohan was ramping up her partying behavior behind the scenes — which might explain the bold choice to forgo wearing any bottoms at her birthday party at the MGM Grand Casino and Hotel in Las Vegas. For her 23rd birthday, Lohan teamed up with Sevin Nyne tanning mist to host an all-out bash. Opting to go for a more "poolside" look, Lohan also chose to party pantsless.

Lohan's love of partying was beginning to catch up with her around this time. In 2007, production for the film "I Know Who Killed Me" was delayed due to the actor needing to remove her appendix, however, she also immediately checked herself into rehab after the surgery. According to People, this not only put the production on hold for quite a while, but also possibly led to Lohan being labeled as unreliable in Hollywood. For several years after this, it seemed Lohan couldn't get cast in any movies — and if she did, there were issues with completing and distributing them. Yet, the star continued to party the pain away.

Coachella was once known as the place to rub elbows with stars, party to live music, and check out what fashion trends might be emerging next. Lindsay Lohan, however, didn't quite nail the assignment. Seen here attending Coachella in 2010, Lohan looks like she threw this look together without thought. The mismatched tie-dye vest, the bandeau, and the acid wash denim shorts look like she was going for "hippie goes to a rave," but ended up just looking like she rolled out of bed. Which just might be the case.

2010 was a bruiser of a year for Lohan. According to the New York Post, right around this time is when she was getting banned from nightclubs and blacklisted from film sets. According to a source who spotted Lohan at Coachella, "Lindsay appeared wasted all day Friday. She looked a mess. Her hair was lanky, she's too thin, and her eyes were glazed. She kept losing her temper over the slightest thing." With reports on Lohan's sketchy behavior escalating, it wasn't long before she also found herself in some legal trouble.

As Lindsay Lohan arrived at court in Los Angeles in February of 2011, her skin-tight white dress showed off her legs, and her attitude. The knit dress, large sunglasses, and black heels combo was not working to make her appear more mindful or put together. Many pointed out it appeared she was rolling into the courthouse looking like she had just spent the night partying. This look was enough to keep her name in the tabloids, but not enough to win her favor with the judge.

In January of 2010, Lohan was accused of trying on a $2,500 necklace from a jewelry store in Venice, California, and then walking out with it still on. For the first portion of her case, the "Herbie: Fully Loaded" star tried to plead not guilty, however, she ultimately changed her plea to "no contest." Switching her plea was admitting she did, in fact, leave the store with the item, without admitting she did it on purpose. The end result was Lohan spent a little over two weeks under house arrest for this crime — however, it was one in a long string of arrests for Lohan.

In 2015, Lindsay Lohan pivoted toward her music career when beloved '80s hitmakers Duran Duran featured her vocals on one of their songs. On the album "Paper Gods," her sultry voice can be heard in the song "Dancephobia," although the actor clearly has no fear of dancing. Seen here stepping out to head into a nightclub in London, Lohan has once again forgotten to put on pants. Her fur coat and semi-sheer dress combination feels off-kilter, even if she did find a hat to match the color. For someone trying to rehabilitate her image after years of party squalor, she certainly chose the wrong outfit for it. Luckily, for the many times Lohan has joined the band on stage, she's always managed to sparkle.

Since the release of "Dancephobia," Lohan has often appeared in the crowd or performed alongside Duran Duran lead singer Simon Le Bon. The song has proven to be a hit, and it helped keep Lohan's head above water while she was navigating her way back to the film industry. With all those tumultuous years, sordid plastic surgery rumors, and inappropriate outfits behind her, here's hoping she can continue to create healthy success for years to come.