Dressing Like Chessy From The Parent Trap (1998) Will Heal Your Inner Child
Embrace the quiet comfort of everyone's favorite supporting character
Lisa Ann Walter’s incredible portrayal of Chessy in The Parent Trap is hardly the only reason to revisit the film. You’re now the age of Meredith! Lindsay Lohan doing a miniature Diane Keaton bit is adorable! The merch for Parker Knoll kind of rocks! But on a gloomy Monday afternoon, I did what any great fashion researcher would do, and shelled the $3.99 to rent the movie on behalf of you, Long Live reader, with one question in mind. How can I dress more like Chessy?
She’s technically hired to help manage Dennis Quaid’s expansive property, but fan theories abound. I don’t really care why she’s in the movie, I’m just grateful she is. Her outfits are very much in the J.Crew 90s catalogue universe, with some distinctly Chessy twists.
Highly practical hair accessories
Chessy is a practical woman. And she notices details. Famously, that the twins are swapped. It’s not like Chessy to mess with French twist clips or ribbons. She has chocolate chip pancakes to make! I love her scrunchie in the scene where we’re introduced to her. She wears a very 1998 hair clip later on, too. I think owning too many hair accessories is a serious cramp on your style. Find a few that feel like YOU and rotate them often. I have a couple headbands, well, dozens of ribbons, but let’s ignore that, and a few clips that I love.
This with a bright pink cotton summer dress…perfection.
A barrette that won’t break the bank. Not everyone is a barrette person! But it’s worth experimenting.
Chessy would approve of the color options and how understated this option is.
Lived-in cotton button down
Everything comes back to this for me. A little oversized. Washed a hundred times. Left to dry on the line. There’s nothing that feels as easy breezy to me as this exact shirt. Chessy favors a solid color. I usually take a stripe. But however you wear it, there are endless secondhand options at your disposal.
This is a great gateway to thrifting IRL. Most thrift stores have entire racks dedicated to these shirts in the mens section. Look for 100% cotton and brands like LL Bean or J.Crew or Brooks Brothers.
Very much what we’re going for here.
Something I’d certainly go for and under $25.
I like a black button down a LOT! The Oxford Big Shirt from Gap is a good place to start if you want to experiment, but are nervous about secondhand.
I have some great vintage Eddie Bauer button downs, too. This one is a large and $30.
Tapered 90s light wash denim
If you need a refresher on how to buy secondhand denim online, start with the letter below. This is your reminder that some eBay sellers accept returns! And if a pair of great vintage jeans doesn’t fit you, it’ll fit one of your friends. It’s a risk and reward dance.
Chessy goes for a light wash and tapered leg, as she should. If you’re new to a tapered leg, it might take some getting used to, but I find the silhouette is super cute with a tank tucked in and a button down undone on top—per our muse.
Here’s a pretty subtle place to start if secondhand denim feels intimidating.
Levi’s 550s are your best bet here. Expect to pay $20-$60 per pair!
Make sure to take careful measurements. If they’re not provided, you can always ask the seller for them! These are 32x32 vintage Wranglers for $60.
Silver statement earrings + silver jewelry at large
Ok, this is going to be a show don’t tell situation. And this has to be vintage, sorry. There are too many great options for way too affordable of prices online for me to let you buy new! Enjoy the following Chessy curation.
90s daisies on a chain for $89
90s shell-ish earrings for $25
Green chino shorts
I think a pair of great green chino shorts can make you feel like you have a completely new summer wardrobe. Pairing options are limitless, one of my favorites being all white or all black besides the shorts. Chessy wears hers in a very nonchalant way. Size up here if you’re between sizes!
Go sportier with these vintage Patagonia shorts!
Vintage Eddie Bauer is a very Chessy search term. These are $30.
I find a leg that widens way more comfortable and balanced with the kinds of tops I’m drawn to. This pair from Frank + Eileen is VERY good.
Bonus points for the built-in buckle! This vintage pair is $27 on Poshmark.
Solid cotton base layers
We’re looking to layer with solid-colored cotton basics to create dimension here. My best bet is that you own these pieces, it’s just time to assign them to some new outfits. I like sticking with colors like red, yellow, blue, white, or grey. And then throw some black, blue, stripes, or white on top. Doubling up on a single color in two different shades is very chic, too.
I’m PICKY about tank tops and rarely wear them, but this tank from Argent really took me by surprise. The color is a layering lifesaver.
Here’s a 90s Gap tank that gives a similar effect.
Look, I’m not happy to share that a $90 tshirt rocks, but it’s the case with this one.
Agnes B. WHO? This is…say it with me…vintage Eddie Bauer and $20.
Vintage Gap tees are worth their weight in gold. This one is $18.
Lands’ End turtlenecks are unmatched.
Button down shirts worn as jackets
This should take only a minute. Put on a tank top. Then a button down. Unbutton it entirely. And tada—you’re Chessy Chic. I like sporting this look over a long swingy dress in the summer or even a tiny mini if I know it’ll be cold inside. Denim is a great place to start, but don’t stop there! Linen makes a wonderful option, as well.
A wonderful denim option under $20 on eBay!
Alex Mill nails the vintage wash.
Vintage J.Jill is the answer. This top is $25.
Fisherman sandals
While we never see Chessy in fisherman sandals, it’s pretty much guaranteed she had a pair or too. Plus, it’s forty degrees in New York, so I’ll take any summer distractions, thank you very much. A great sandal is hard to find. I like mine to be very walkable but not too chunky. I’ve purchased a few pairs secondhand. It’s a gamble! But I usually spend under $20, so not that much of a gamble.
This color is immaculate, right? I’d wear with sundresses and the rest of my Chessy closet.
I’ve tried for so many summers to be a Birkenstocks girl, but it’s not in the cards for me. These are very elevated, begging to be worn with an all-white cotton look.
Loeffler Randall makes great sandals. So great, in fact, they hold up on the secondhand market! These are 11.5 and $70 on Poshmark.
Honorable Mentions
I’m hosting an IRL vintage sale with Rothy’s! Everything is under $100. It’ll be SUCH a fun morning. RSVP here :)
The Ballad of Wallis Island is just the movie to watch on a rainy Saturday afternoon.
Another banger Money With Katie episode, this time on fashion and class.
I replaced my bedside lamp with this bulb in January and have never looked back.
Thank you for reading Long Live. It means so much to me. You can preorder my romance novel, Exit Lane, on Bookshop or Amazon. You can shop my favs here, follow along on Instagram + Tiktok, and shop my Notion template. Get matched at EV Salon. And if you want to partner on a future Long Live, email evan@communite.co x
For inexpensive, walkable fishermen's sandals I was about to recommend Salt Water ... but I see that they have wildly raised the price since I bought my pair (which I wear so much) in 2011. So, still walkable but not $24 anymore, damn it.
This piece is hilarious. Thank you.