#42: Style Inspiration from The Parent Trap
The outfits are perfection.
Hi friends-
I posted a note last week after watching a movie with my three boys:
Well, here we are!
The year is 1998. Lindsay Lohan is giving the performance of her life, twice. The movie is a remake of the 1961 classic. And the outfits are the perfect inspiration for 2025.
Let’s revisit the Parent Trap! LL version (obvi!).
This now iconic movie marked the directorial debut of the Nancy Meyers , who was nominated for an Academy Award for Best Original Screenplay for Private Benjamin (1980), co-wrote Father of the Bride, and both wrote and directed Something’s Gotta Give, The Holiday (!!!), It’s Complicated, and The Intern, among many others.
In addition to their cult rom-com statuses, Meyers’ films are justly celebrated for their gorgeous interiors. Emily Henderson, one of my favorite design bloggers, perfectly described Meyer’s film interiors:
It’s giving “I’m rich, but humble” and “Yes, I hired a decorator but want people to think I did this myself.” And I think that’s what we all love about it. Jon Hutman and Beth Rubino, two of Nancy’s go-to production designers, have figured out a way to create rooms that are nostalgic without being dated. Layered without being cluttered (well, it depends on who you are, I guess). Whoever lives in these rooms cares nothing about being “cool” because the rooms aren’t cool. What they are is welcoming, inviting, and just designed enough. And while yes, these are spaces created for movie characters with obvious wealth, they’re still packaged up to feel relatable and warm, almost as if you too might someday find your secret twin sister and swap your Napa ranch for her enormous London estate.
I’d say the same applies to the costume design in The Parent Trap, especially the sense of nostalgia, layering, and being just designed enough.
But don’t take my word. Take Nancy’s1:
I always like to dress my characters simply, in classic silhouettes, and not in too much color. I just want everything on the screen to last and not date itself.”
Penny Rose was the costume designer for the movie (she’s best known for the Pirates of the Caribbean movie), and she created a visual feast of simple, classic style that emphasized each character’s distinct personalities while also showing the connective threads (pun intended) between the different permutations of families and relationships.
How Chessy and Nick dress alike, and how Elizabeth does, too, once she’s in Napa. The shared color palette between Hallie and Annie, despite the very different styles (tomboy vs. tailored). How Meredith sticks out, literally and visually, from the rest of the family (Or does she? More on that below!)
This movie is a masterclass in set and costume design.
It is also a masterclass in style inspiration for today. As I rewatched with my three little boys (who couldn’t get enough of the camping trip gone awry), I had to sit on my hands to keep from pressing pause on the remote. I wanted to take a photo of every scene!
The outfits were shockingly similar to what I’ve been screenshot-ing and saving in my 2025 inspiration folders, adding to my wishlists, and actually buying.
Chocolate brown? Check. Denim shirts? Check. Plaid ala
’s country cowboy trend? Check. Sumptuous suede? Check. Simple styling tricks like wovens over tees and tees under cable sweaters? Check and check.Enough chit-chat. Wanna see what I mean??
Let’s dive in!
The Parent Trap (Lindsay Lohan version, duh) Style Moodboard 2025
THE ICON
All About the Button Down
The look of the movie is the button-down shirt worn open over a tee shirt (or maybe a henley, if Penny Rose was really feeling wild!). I think almost every character at some point wore their own version of this. Except for Meredith, of course.
Outdoorsy plaid shirts, classic oxfords, Western-style denim shirts, soft chambray, linen. The inspiration in this movie is almost endless, or at least in nearly every scene.
The whole vibe is casual, but never boring. As if to say, we are too busy tending to our vineyard, going on a camping trip with an ex, managing a household for a hapless single dad while pseudo-mothering an adorable 11-year-old, or trying to get our parents back together, to care about what we’re wearing, yet we still look completely put-together, comfortable, and cool.
That’s the power of this layered look.
Ralph Lauren’s aesthetic is all over this movie, so much so that I tried to research whether the designer or the company had supplied any of the shirts for the film. (I couldn’t find an answer but I did find out that there was a handshake choreographer on set for Annie and Martin’s secret handshake!)
While almost any RL shirts would give us the look we’re going for, one of my fave Fashion writers,
swears by Frank & Eileen shirts, whose iconic item is a perfect relaxed button-up shirt (did you know it’s technically only a button-down shirt if the collar buttons down?) that I think totally captures the Parent Trap vibes we want.(
is also the best thrifter on Substack, along with . Subscribe to them both, if you don’t already!)
THE COLOR STORY
Chocolate brown is definitely the color of the movie. Or at least of Nick Parker. Perhaps to emphasize his warm and cuddly dad vibes? His down-to-earth nature while somehow also owning a palatial Napa vineyard? The perfect shade to set off his crinkly eyes? We’ll never know for sure, but I do know that it’s an excellent color and one that will continue to carry us through 2025.
Shades of Sorbet
We’ve been talking a lot about a particular shade of powder pink, first spotted by
and recently highlighted in Puck by . Lots of brands are making lemonade out of lemons, and I’ve got my eye on matcha as another color to soak up this spring. Of course, these colors were delicious ingredients for many of Hallie’s and Annie’s looks in the film. Sweet, but not too sugary.
(Speaking of headbands, they might have been the defining accessory of this movie, after the oval sunglasses. I’d bet there was a heavy dose of Carolyn Bessette Kennedy on Penny Rose’s mood board.)
Sporty (and Rich)
I’d also bet money that
had Hallie on her mood board when she created her brand, Sporty and Rich (wanna confirm or deny, Emily??). The tomboy-meets-California laid-back prep is such a seductive style. (It’s also essentially my style, with a heavier dose of New England.) Always was, always will be. Maybe I have to thank Hallie for that?!Tomboy Prep
How cool were these twins? Brave, creative, a little bossy. I still want to be them.
The Bandana
I love a bandana so much I wrote about the history of it. Of course Hallie and Annie pull it off perfectly. (With their plaid and chambray shirts and tees, obvi.)
Here are some bandanas I adore (all $50 or under):
The Henley
Ok. Guys. Look at this cute family in their matching henleys and cohesive palette. Hallie and Annie “match” in shades of coral. Nick and Lizzy “match” in blue-grays. They are soclose to being all back together. Just need to get Lizzy to take the last step from shift dress to button-down shirt to henley to complete the journey.
Despite my best efforts, I could not find the kind of henley we deserve, with a chunky placket, perhaps even a woven one. Garment-dye would be nice, to give it that soft, beloved effect. And we really need a slub fabric, not a waffle, which takes the henley straight into jammie territory.
Since we’re still riding the wave of sweater polos, I think the henley has yet to truly hit. But it’s coming, mark my words. Here are a few options worth checking out:
This one ($165) has a wide placket I like, but I don’t love the wide ribs.
I love how they styled this ($135) with a button-up, olive green track pants, and a denim blazer (even though I’m not a fan of the waffle).
Honestly this kid’s style ($30) comes the closest to my ideal henley, maybe try in a size 14-16??
Last, but certainly not least…the Queen Bees
I’ll be honest, upon rewatch, I seriously judged Nick for meeting, dating, and proposing to a brand-new woman while his daughter was away at camp for what, 8 weeks, max???
But as I thought about Elizabeth and Meredith’s looks for this post, I was surprised that they dressed more similarly than I expected, at least in the beginning of the movie. They both favor sleek little shifts, LBDs (try this one or this one for that iconic 90’s spaghetti strap look), relaxed trench coats, and buttery blonde bobs.
And they’re both strong, determined women with impressive careers.
Perhaps we’re meant to realize that Nick has been chasing versions of Elizabeth ever since they broke up? And that’s why he proposes to Meredith so quickly??
The differences between them, of course, are revealed at the end. First by Elizabeth’s adoption of the unofficial Parker Knoll uniform of soft button-down shirt while Meredith continues to stick out in black spandex (but we can all agree Meredith’s Prada nylon backpack was perfection, just maybe not for a hiking trip).
And then by Meredith’s ultimatum:
“It’s me, or them. Take your pick.”
Without so much as a breath (excellent acting, Mr. Quaid!), Nick answers:
“Them.”
Duh.
And we continue to choose them twenty-seven years later in this gem of a movie and style bible for how we all still want to dress.
(One more thought about Elizabeth. I’d always read that Mary Kate and Ashley Olsen’s first brand (pre-The Row), Elizabeth and James, was named for their siblings. But who thinks perhaps they were as enamored and inspired by Ms. Elizabeth James, wedding dress designer extraordinaire (fun fact: Vera Wang actually designed the gowns!), from this movie, as all of us fellow elder millennials were? The timing works. They are the other most famous (real life) twins of the 90s. Methinks there’s a story there!)
Want to read more behind-the-scenes?
featured the movie in her film-focused substack:
Before we go,
shared the master spreadsheet of GoFundMes for Black families who were displaced by the Eaton fire and the giant spreadsheet of GoFundMes for people impacted by both Eaton and Palisades fires. For those in L.A. or with friends or family there, Lily and Hopie Stockman have converted their Block Shop Textiles store in Atwater Village into a community space for anyone who needs a comfortable place to rest, with WiFi, childcare and activities, and snacks. Avery Colvert, an eighth grader in Pasadena, started a donation drive (NY Times gift link) called Altadena Girls that has been collecting and dispersing items specifically for teenage girls who are victims of the fires.If you know of anyone who needs our help, please drop a note in the comments.
Thank you, as always, for reading. I loved writing this one, I got to return to my college costume design roots. I hope you enjoyed it!! Tell me in the comments, are you a Hallie? Annie? Elizabeth? Chessy? Meredith? (Apparently, they’re BFFs in real life!) Nick? A combo of all of them? I want to know!!
x Lindsay
https://www.cntraveler.com/story/what-to-wear-in-london
Brilliant, brilliant breakdown. Your quote from Nancy Meyer struck me; classic silhouettes that remain timeless. Of course the costumes are still relevant and inspirational. But rather than a boring sort of timeless there is a feminine touch from the pastels or a masculine vibe from the sporty moments; it’s proof to me that we can have wardrobes that can age well while expressing our POVs!!
I will never not love this movie! This was such a fun read!!