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Lindsay Lohan Pulled Two Major ‘Parent Trap’-Inspired Looks

Key Takeaways
- Lindsay Lohan wore a pair of outfits inspired by her starring role(s) in 1998’s The Parent Trap.
- The plaid skirt suit (with a matching headband!) and silk minidress were both perfect in their own ways—Annie and Hallie would be so proud.
I’ve done a lot of complaining about how every movie that comes out or look that someone comes up with these days is pure nostalgia farming. I still believe this is true, but I want to rescind (most of) my protests. Now that we’re referencing art I care deeply about… I kinda like the callbacks.
Today, Lindsay Lohan stepped out in New York wearing *two* outfits that were purposefully Parent Trap-coded—one for each twin she played in the 1998 movie, naturally. The looks were part of her Freakier Friday press tour, but that doesn’t matter; I’ll take an homage to any early aught’s LiLo production.
Lindsay Lohan’s Annie James Plaid Outfit
@lindsaylohan/Instagram
For her first look, Lohan gave the posh twin, Miss Annie James, some time to shine stateside with a yellow-and-black plaid Balmain mini skirt suit. She paired it with a headband which pulled back her pre-camp-haircut lengthy locks for even more “Annie James energy with a Freakier Friday Twist.”
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The 39-year-old took the outfit to Good Morning America, where she talked about how fun it’s been to work with Jamie Lee Curtis again. Trust me, diva, it’s been even more fun to watch it. And you’re making it all the better.
Lindsay Lohan’s Hallie Parker Silk Dress
For her next look, Lohan wore a traditional Chinese qipao or cheongsam-inspired Roberto Cavalli minidress just like the one Cali twin Hallie wore when orchestrating her parents’ reconnection via romantic boat dinner in the ’98 masterpiece. This version featured cap sleeves, gold buttons, and lots of color.
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“A little shine, a little silk, a lot of love and some inspo from Hallie Parker,” she captioned an Instagram post showing off the look. She skipped the chopsticks in her hair, once again opting for long waves that showed off her “soft gloss blonde” hair color.
@lindsaylohan/Instagram
“Your daddy took me riding the other day and he let me ride your horse. I hope that’s okay with you,” commented Elaine Hendrix on the post.
Hallie probably minds, but it’s soooo okay with me. Now, how about a Confessions of a Teenage Drama Queen-themed styling day? Things are getting freaky in the best way possible.