Lindsay Lohan Recreates Parent Trap Looks 27 Years Later

Lindsay Lohan channels Annie and Hallie from The Parent Trap with two nostalgic fashion tributes during her Freakier Friday press tour.

Lindsay Lohan is taking a stylish trip down memory lane—and fans of The Parent Trap are loving every second of it.

While promoting her upcoming movie Freakier Friday, the sequel to the beloved 2003 comedy Freaky Friday, Lindsay Lohan delivered a double dose of nostalgia by recreating two of her most iconic looks from the 1998 film that launched her career. On Monday, July 28, she paid tribute to both Annie James and Hallie Parker, the twin sisters she famously portrayed in The Parent Trap, with updated fashion moments inspired by their original styles.

During an appearance on Good Morning America, Lindsay Lohan stepped out in a modern take on Annie’s polished British look. The ensemble—a butter yellow two-piece set from Balmain’s pre-spring 2026 collection by Olivier Rousteing—included a tweed jacket with a white and black plaid pattern and a matching miniskirt. The outfit gave a subtle nod to Annie’s signature yellow cardigan and her memorable plaid ensemble from the film, while also evoking a hint of Clueless-era chic.

Later that same day, Lohan appeared on Live with Kelly & Mark wearing a second homage—this time inspired by her character Hallie Parker. She donned a fitted, cheongsam-inspired minidress by Roberto Cavalli, featuring a mandarin collar, corset-style waist, and a vibrant pattern with tropical birds, flowers, and branches. The look clearly echoed Hallie’s soft pink cheongsam-style dress from the movie, right down to its delicate, feminine detailing.

These throwback outfits arrive just days after Lindsay Lohan reunited with Parent Trap co-stars Lisa Ann Walter and Elaine Hendrix at the Freakier Friday premiere in Los Angeles on Tuesday, July 22.

Freakier Friday hits theaters on Friday, August 8, marking Lindsay Lohan’s return to the genre that helped define her early career—and she’s clearly embracing the full-circle moment in style.