Lindsay Lohan's Most Iconic Outfits That Scream Outdated Today

No one owned the 2000s like Lindsay Lohan. From the comedy classic "Mean Girls" to her debut album "Rumors" to paparazzi shots of her shopping at Kitson, the casually sexy and relentlessly charismatic Lohan was an icon. Few stars better embodied the style of the era; in part, that's because Lohan defined the aesthetic. She wasn't merely copying 2000s style trends; she was setting them, sometimes with the help of celebrity stylist Rachel Zoe, who counted Lohan among her most high-profile clients. "I am the biggest fashion-obsessed person in the world," Zoe told The Seattle Times in 2005. "But in Lindsay, I feel like I may have met my match. If she wasn't an actress, she would be a stylist, because she would have to be."

Lohan winked out of the public eye for many years, but her recent renaissance has made one thing clear: her charm has staying power. Still, it's hard to overstate just how iconic her throwback looks were. We're not exactly looking to wear these styles today—even Lohan has undergone a head-turning transformation and updated her style — but we're still nostalgic for Lohan's cultural heyday, when she was serving Marc Jacobs purse after Valentino dress.

There were prom vibes to the strapless, puffy-skirted dress that Lindsay Lohan wore on the red carpet for the 2007 premiere of "Georgia Rule." The frock perfectly suited then-trends, which favored shorter lengths, even for formal occasions, and an 80s-inspired silhouette. Today, we might expect a star like Lohan to opt for something floor-length that flatters her vertical line, but back then, this party dress would have been all the rage.

In roughly 2008, Lindsay Lohan began working with celebrity stylist Rachel Zoe, who was famous for her signature boho-glam style that dominated fashion in the late 2000s. Lohan was one of her most fervent disciples. When she stepped out at the "Mr & Mrs Smith" premiere wearing a bombshell Gucci gown, it marked the beginning of a new style era — more sophisticated and overly sexy. But to modern eyes, this look is very of its moment. The platinum blonde hair and lingerie-inspired gown suit the overt sexiness that then dominated fashion, which has since shifted toward more modest, elegant styles.

Lindsay Lohan served pure maximalism for a 2009 appearance at Bloomingdale's. The style, with its fusion of boho and rocker glam, would have been completely on trend in the late 2000s as fashion shifted toward the casual sexiness of indie sleaze. From the long, layered necklaces to the black fedora to the sky-high booties, Lohan looks like she belongs at an Arctic Monkeys concert. Today, these super skinny legging-pants are out in favor of looser, oversized trousers.

From the plunging neckline to the dramatic sparkles, Lindsay Lohan served major glam at the 2010 MTV Movie Awards. The silhouette feels 70s-inspired and we can totally imagine this mixed-metallics jumpsuit at Studio 54. That decade was enjoying a major fashion revival when Lohan wore this piece, and 2000s trends are very informed by the disco era. But, most of all, nothing says "throwback to the 2000s" like a major sparkle moment or copious cleavage. It's a little over-the-top for today's minimalism moment, but Lohan looks like the Y2K icon she is.

Lindsay Lohan donned skin-tight black jeans to attend a collection preview of by designer Rebecca Minkoff. Of course, it's possible to style skinny jeans so you don't look outdated, but Lohan's ensemble is peak 2010. From the platform, stiletto heels to the close-fitted moto jacket, this is a major indie sleaze moment. It's giving high fashion meets rocker chic — cool at the time, but seriously out of step with modern trends that are more polished and minimal.

Fashion icon Karl Lagerfeld lent his expertise to this look, which Lindsay Lohan wore for a Chanel Ready To Wear show in Paris in 2010. Besides the era-appropriate skinny jeans, the ensemble included a few 2010s accessory must-haves: a handband, a looped skinny scarf, and a platform pumps. The rock and roll look appears seriously casual to the modern eye, but Lohan revealed this styling was not only Lagerfeld-approved—he had a hand in creating it. "I went backstage and he just started layering me," reminisced the actress during a 2022 interview with Vogue.

Lindsay Lohan was channeling peak party Millennial when she stepped out in L.A. wearing leather shorts, a graphic tee, and an oversized purse. The shorts-as-evening-wear feels straight out of indie sleaze Bushwick, and the big statement purse is a staple of the Rachel Zoe aesthetic. This look would have been fashion forward when Lohan wore it in 2010, but it looks tired now, since trends have pivoted toward microbags. And, instead of shorts, we're looking for grown-up ways to participate in the mini skirt revival.

During Paris Fashion Week in 2012, Lindsay Lohan donned a pair of seriously oversized sunglasses. These bug-eyed specs were a redux of 60s and 70s trends and were everywhere during the 2000s, another Rachel Zoe influence that proliferated all over Hollywood. Today, these shades immediately date Lohan's outfit, as does the above-the-knee skirt. One trick for avoiding sunglasses that will date your look is to find the sunglass silhouette for your face shape. Flattering shapes will always be timeless.

The oversized graphic tee that Lindsay Lohan wore for the 2013 Z100 Jingle Ball is giving serious indie sleaze. The oversized shirt styled as a dress belongs in an era when it was considered the height of chic to look like you'd been caught stumbling home from a fabulous night at the club. The long, tousled hair and knee-high boots perfectly complete the ensemble. It might have been on trend at the time, but looks a little rumpled and understated to modern eyes.