Lindsay Lohan Relives Her Life in Looks, From The Parent Trap to Mean Girls

“Why am I wearing flip-flops and a scarf?” This is what Lindsay Lohan ponders as she looks back at a casual outfit she wore back in 2002, when she attended the Neil Bogart Memorial Fund’s Annual Tour for a Cure in a blue Juicy Couture sweatsuit. The actor may be unsure of this particular look now, but over the course of over two decades in the business, Lohan has had many fashion wins, too. In a new video, she sat down with vogue to relive some of best style moments on and off the big screen.

Lohan begins her fashion flashback by taking in a blue Nicole Miller dress she wore to the 1998 premiere of The Parent Trap, her first feature film that she starred in when she was 11. “My mom still has this dress. She kept it for me at home,” says Lohan. “As a young girl, I was always really into fashion.” Playing dress up on the red carpet is something Lohan only took to the next level during her career. Another personal favorite of hers was in 2006, when she wore a vintage Versace gown to the Vanity Fair Oscars party. “They stitched the dress onto me, because it was so delicate and dainty,” says Lohan. “I loved the glamorous Old Hollywood.”

It wouldn’t be a true Life in Looks video if Lohan didn’t explore some of her best ensembles worn in her films as well. She remembers rocking the baggy pants and chunky highlights in 2003’s freaky friday. “I was really rocking the Avril Lavigne vibe, because that was my character, and I really took it into my daily life,” she says. The bold, Y2K pieces she wore in 2004’s Confessions of a Teenage Drama Queen were equally memorable. “This was when I was like, ‘Please dress me like Britney Spears.’ It was that whole era of Britney.” And who could forget her transformation into one of the pink-wearing Plastics in 2004’s Mean Girls? “I wanted to play Regina,” Lohan reveals. “I had just come off of freaky friday, and I really wanted to play a pretty, normal girl. I [didn’t want] to be the damaged teenager again!”

As for more recent fashion memories for Lohan? She reminisced on attending the fall 2010 Chanel show with the late designer Karl Lagerfeld by her side. “If there’s someone I really miss, it’s Karl Lagerfeld,” she says. “Whenever I was in Paris, Karl was like a father to me—he really took me under his wing.” She also attended Saint Laurent’s show with her brother, Dakota, in 2019. “My brother and I had the best time,” says Lohan. “My family is so important to me, so anytime I have an opportunity to involve my sister, brother, and my mom in anything that I do, I always jump at that.”

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