Lindsay Lohan Red Carpet Looks We'll Never Forget

As one of the most recognizable faces of the 2000s, Lindsay Lohan's sartorial moments — good and bad — were legendary. She was peak Y2K, whether she was wearing a trucker hat on the red carpet or collaborating with decade-defining celebrity stylist Rachel Zoe. For many years, though, Lohan has been out of the spotlight. It was time that allowed her to build an intentional life, connected with who she really is. "I was like, 'What if I never fall in love? What if this never happens? And it took me just taking time for me for all those doors to open and the 'yeses' to come — the things I wanted to say 'yes' to," she told Bustle in 2024.

Now, a more-grounded Lohan has returned to the screen in recent years with a cameo in the "Mean Girls" reboot and three Netflix movies: "Falling for Christmas," "Irish Wish," and "Our Little Secret." As she stepped out to promote her recent films, the star looked more stunning than ever, and it's got us thinking about her greatest red carpets hits. Lohan might just be the ultimate millennial movie star, and her elegant, vintage-inspired style has given us plenty to celebrate.

At 12-years-old, Lindsay Lohan shot to fame when she played the dual roles of precocious twins Annie James and Hallie Parker in the 1998 remake of "The Parent Trap." Her first-ever red carpet look was simply adorable, with low strappy heels in a Y2K iridescence and a simple blue shift dress with embroidered detailing (more Annie than Hallie, in our opinion). The sweet look was a preview of the red carpet powerhouse she would become. She's also called back to those characters in plenty of style choices since, channeling each twin on the red carpet.

This ensemble from the 2003 MTV Video Music Awards is peak style in an era when denim was appropriate for literally everything. Ripped jeans on the red carpet? Go for it! Lindsay Lohan dressed up her distressed flares with sultry black bustier layered over a white collared shirt, pointed-toe heels, and some mega-Y2K shades.

Also on display? The first of many hair transformations the iconic redhead would undergo over the years.The star stepped out with a strawberry blond tone and thick fringe.

The 2004 "Mean Girls" premiere caught Lindsay Lohan in between her teen star and full-blown movie star days. The demure, knee-length dress in a bright turquoise, paired with strappy, silver sandals, accentuates her 2000s-era tan. The side-parted hair? Iconic. While the A-list star wasn't quite on the top of her fashion game yet, there's a real innocence to her styling here.

Lindsay Lohan got an obvious glow up when she appeared at the red carpet premiere of "Mr & Mrs Smith" in a fitted Gucci dress, towering Chloe heels, and freshly platinum-colored locks. Lohan's transformation into total movie star was the handiwork of celebrity stylist Rachel Zoe, who began working with the "Mean Girls" actress in 2004. 

Zoe was responsible for the bohemian-esque versions of 1970s glamor that had Hollywood in a chokehold during the early aughts, and she refined Lohan's bohemian instincts to make her one of the decade's most imitated fashion figures. In an interview with Vogue (via The Guardian), Zoe described her signature style as "very '60s to '70s glamour. It's Mod meets Grecian. A lot of gold and a lot of bronze, shimmer and glamour, but relaxed glamour."

This gorgeous 2024 look gave all the comeback vibes. Lohan wore this Zuhair Murad gown, with its silver-accented bodysuit and sheer maxi skirt combo, for the premiere of her new Netflix Christmas movie, "Our Little Secret." From the classic black to her elegant blonde waves, Lohan looks to be at the height of her movie star powers. 

Her career reboot has been slowly building in recent years, in part thanks to the 2022 release of "Falling for Christmas." This look harkens back to the Grecian-inspired styling of her Rachel Zoe days. With a red carpet look this sophisticated and sultry, it appears she's back, baby.