Lindsay Lohan has been acting since her commercial and soap opera beginnings in the early ’90s, and, of course, she broke big at the age of 12 when The Parent Trap came out in 1998. That means she has a whole fashion history filled with red carpet premieres, and each look represents a new phase in her career. So, while promoting the Freaky Friday sequel Freakier Friday, Jimmy Fallon busted out a picture of Lohan from the 2003 movie’s premiere, and she was actually her own worst critic.
Being in the movie industry since childhood, Lindsay Lohan’s fashion journey has evolved dramatically from playful red carpet looks to a more adult, sophisticated style. When she appeared on The Tonight Show to promote her 2025 movie release, Freakier Friday, Jimmy Fallon busted out a photo of Lohan from when she attended the OG Freaky Friday premiere. Surprisingly, she was quite critical of herself, saying:
Way too much black eyeliner…
I happen to agree with Jimmy Fallon that I thought Lindsay Lohan looked great! In the throwback photo, the Georgia Rule actress wore a gold metallic dress and sported auburn hair with bangs. And the smoky eyeliner she had on really made her eyes stand out. Plus, when I grew up in the 2000s, many teen girls rocked the dark eyeliner look, including me, and honestly, I’m still here for it.
If you need a reminder of Lohan’s teenage Freaky Friday premiere look, check out her cute photo with Jamie Lee Curtis below:
Aww, I love seeing Jamie Lee Curtis and Lindsay Lohan hand-in-hand, head-to-head in the OG photo like a mother/daughter pairing would be. Their effortless chemistry made Freaky Friday as memorable as it was, and that’s thanks to their heartwarming moments and remarkable comedic timing that came when they switched bodies.
Getting to see Jamie Lee Curtis and Lindsay Lohan back in action for the sequel is what I look forward to seeing in the new movie the most. The former child star told Jimmy Fallon that the idea of Freakier Friday began when Curtis was asked about it while promoting Halloween (2018), and that sparked questions for Lohan, too. Given the mother-daughter chemistry the pair had in the 2003 Disney flick, it’s no wonder fans were rooting for this movie to happen.
Now, the movie is almost here, and Lindsay Lohan is back on her red carpet A-game.
While she didn’t wear any thick black eyeliner for the Freakier Friday premieres, she still threw back to her nostalgic signature looks. At the UK premiere, she went full method-dresser, wearing a lavender dress that looked just like the one Anna wore in the final wedding scene of Freaky Friday. And that cute little guitar purse was the perfect homage to her character’s rocker roots.
Meanwhile, at the Los Angeles and New Mexico red carpet launches, Lindsay Lohan was fully embracing Barbiecore, wearing different shades of pink gowns. It was a playful nod to Y2K fashion that showed her mature, glamorous style while still having fun with each look.
Lindsay Lohan may have cringed at the black eyeliner she wore at the OG Freaky Friday premiere, but it perfectly captured the edgy, early-2000s teen spirit she embodied at the time. Fashion is always a good way to travel back in time and reflect on the trends, moods, and attitudes of a particular generation. Now that Lohan is an adult, I’m certain she’s got plenty of classy, poised looks she’ll adorn at future premieres.
Make sure to see Freakier Friday in theaters on August 8th.