Lindsay Lohan Throwback Photos

Lindsay Lohan is all grown up, but her child stardom lives on in her films and photos.

It's hard to forget the bubbly 12-year-old who stole hearts worldwide for her doubly good performance in The Parent Trap. In the years that followed, Lohan became a Y2K style icon for teens around the world, setting trends at star-studded events throughout her youth.

As a 38-year-old today, the Mean Girls star is settling into parenthood alongside her husband, Bader Shammas. But we can still look back on the years that launched Lohan's enduring career in Hollywood.

See some of Lindsay Lohan's cutest throwback photos from her teen years and childhood.

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'The Parent Trap'

At just 12 years old, Lohan became a massive star thanks to her breakout role in Nancy Meyers' 1998 remake of The Parent Trap. The young actress played twins Annie James and Hallie Parker, doing double the work in her portrayal of the British and American long-lost siblings.

On the movie's 23rd anniversary in 2021, the former child star celebrated the movie with Meyers on Instagram. In the comments of the director's commemorative post, Lohan thanked her and called the movie "the opportunity of a lifetime."

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Family on Set

Dakota Lohan; Lindsay Lohan — Dakota Lohan and Lindsay Lohan in the 1990s. Lindsay Lohan Instagram

Lohan and her little brother, Dakota, snapped an adorable shot in London while she was shooting the The Parent Trap. The sibling duo returned to the spot to remake the photo in 2022, about 24 years later. The only differences were that Lohan wasn't in costume as her character Annie, and this time it was Dakota doing the lifting!

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First Premiere

Lohan wore a white and blue dress to the summer premiere ofThe Parent Trap. In 2022, Lohan reviewed some of her style highlights over the years with Vogue and revealed that her mom, Dina Lohan, still has this Nicole Miller number.

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Sweet Smile

Lohan's style might've evolved over the years, but her smile has stayed the same.

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'Life-Size'

The TV movie Life-Size premiered on ABC in 2000 and starred Lohan as Casey, a girl whose doll (played by Tyra Banks) comes to life.

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'Freaky Friday'

In 2003, Lohan starred as Jamie Lee Curtis' daughter in Freaky Friday, her second ever feature film appearance. Lohan was only 16 years old when she played rebellious teen Anna Coleman, who is forced to see things from a new perspective when she and her mother switch bodies.

The former costars reflected on the hit Disney remake in 2023, speaking to The New York Times in honor of the movie's 20th anniversary. Lohan remembered how Curtis "immediately took me under her wing" and even helped with an especially nerve-wracking scene.

"I was so nervous to do my first kiss on camera, so she talked to me in my trailer and made it funny so that I wouldn't stress about it," Lohan recalled in the retrospective interview. A sequel is now in the works with both stars on board.

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Model Behavior

In honor of Easter 2022, Lohan resurfaced an old photo of her posing for children's fashion magazine Earnshaw's. She looked precious in a flower headpiece and a spring-patterned dress. Fitting with the holiday's theme, Lohan held a white rabbit in her hands, a striking contrast against her signature red locks!

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Flashing Back

In an equally adorable throwback photo, a young Lohan wore pigtails and jeans. She shared the snap on Instagram as a "#FlashbackFriday" post in 2022.

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On the Carpet

After breaking into the industry with The Parent Trap, Lohan started taking red carpets by storm. In 1999, she attended the New York City premiere of Anywhere But Here.

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Showing Up Everywhere

Lohan supported her Parent Trap costar Dennis Quaid (who played her dad) at a screening of his HBO comedy Dinner with Friends in 2001.

Years later, Quaid praised Lohan for her earliest movie performance as twins Annie and Hallie: ��She had me believing they were two different kids. She was a savant,” Quaid said on The IMDb Show in 2019. “She could just channel anything like that. Some people are like that and the rest of us have to work at it.”

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Growing Up

In a tie-dyed tee and bright blue choker, Lohan looked like the picture of Y2K style when she attended the Ice Age premiere at age 15 in 2002.

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Teen Star

With her famously fiery locks and freckled face, 15-year-old Lohan doesn't look much different from the 38-year-old she is today.

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Style Evolution

Lohan did eventually dye her hair from its natural red after her teen years, a time when her life "was changing for fashion," as she told Vogue.

"No one wanted me to dye my hair blond," she recalled during a 2022 interview for the magazine's Life in Looks series. "Everyone was like, 'Do not do that. You're going to ruin your red hair,' — especially my mom. And this is the problem: when you go from red to blonde and you do it in a rush, it goes yellow. And that's a true, hard fact."