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Enter Your Chessy Era With These Parent Trap-Inspired Outfits

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Chessy from The Parent Trap lives with Nick Parker in Napa Valley with a golden retriever and a super chilled wardrobe - what more could you ask for?

Chessy parent trap outfits.
updated on:
October 24, 2022

One of the most nostalgic comfort movies from the late 90's has to be The Parent Trap starring Lindsay Lohan. From Camp Walden to sunny California to beautiful London, The Parent Trap takes us all right back to the warm-fuzzy romantic comedies of that era.

Over the years, The Parent Trap has been examined and reexamined for all its worth: why Meredith Blake was wrongfully painted a villain, how Natasha Richardson's character Elizabeth James reminded us all of Princess Diana, and that a bridal hat moment will always be iconic. But there is one hero that has yet to have her moment: Chessy! The housekeeper/chef/nanny/friend of the Parker household.

Chessy's style is laid-back, late 90's, California Adventure chic. Her outfits are functional, but never stuffy. From chasing Sammy and Hallie around the vineyard grounds, to cooking up some bomb chili, to bringing Nick Parker dirty martinis on the patio, Chessy's outfits perfectly blend with her surroundings, while making her look and feel like home.

Whether you're looking to start your Chessy era, or need some ideas for a Parent Trap Halloween costume, here are some Chessy Parent Trap outfits from Amazon!

This post is all about chessy parent trap outfits.

Chessy's Wardrobe Staples

Oversized Button Downs

Chessy absolutely ROCKS a classic men's-size button down. She typically opts for neutral shades and the more oversized the better!

White

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Striped

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Green

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Chambray

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Flannel

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Corduroy

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Tank Tops

Chessy usually keeps it classy by wearing neutral colored tank tops under her oversized button downs!

Neutral Camis

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V-Neck Camis

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Square Neck Camis

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High Neck Camis

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Khakis

Chessy's khakis are functional and comfy! Perfect for multi-tasking.

Dickies

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Cargo

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Jeans

You can't go wrong with a pair of 90's-inspired Levi's. They're quintessentially California.

Levi's

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Shorts

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Overalls

Chessy doesn't technically wear any overalls in the movie, but don't you think she would rock them anyways? Maybe she wears them during her time off...

Full Length

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Shorts

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Gold Mini Hoops

Chessy wears some simple gold dangly earrings in the movie, but I could totally see her wearing mini gold hoops to add a little something to her daily uniform.

Stud

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Huggies

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Claw Clips

Chessy needs claw clips to keep her hair out of her face when she's taking care of the Parker household! Here are some options for every hair thickness!

Medium

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Large

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Extra-Large

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Casual Shoes

Chessy's shoes are not highlighted very much in the movie, but I would guess that her shoe taste is very similar to her clothing taste - simple, comfortable, and functional!

Birkenstocks

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Loafers

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Cowgirl Boots

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Sneakers

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If you like this post you may enjoy this post: Iconic 90's Pop Culture Halloween Costumes For Every It-Girl

Chessy's Favorites

We really didn't get enough Chessy screen time in The Parent Trap, so I've decided to imagine what some of Chessy's favorite products would be! These would make perfect gifts for your friends who have a similar style to Chessy or for yourself if you want to emulate some of Chessy's many wonderful qualities!

Aesthetic Wine Glasses

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You know that the Parker household is bound to have the latest and greatest wine-tasting technology around, and the most trendy and aesthetic wine glasses. Chessy would definitely be more of a stemless girl, but these wine glasses are just so cute I bet she would have them in her kitchen.

Ray Bans

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Chessy needs a good pair of sunglasses for when she's driving around the vineyard. These are perfectly feminine and masculine which is totally Chessy's vibe.

Le Creuset Bundle

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Chessy apparently makes some amazing chili. So much so that when "Hallie" turns down her favorite meal, Chessy knows something is up. You already know Chessy's kitchen is stocked with the best cooking stuff so she would definitely have Le Creuset.

Green Striped Pool Towels

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Hallie is always splashing around in the pool. I'll bet Chessy lounges around once in while - when she's clocked out of course!

Messenger Bag

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I just know that Chessy is the "mom friend". She keeps everything prepared just in case of emergency. This messenger bag seems totally like her.

Golden Retriever Socks

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Of course Chessy's favorite dog is a golden retriever because of the Parker's dog Sammy! I bet she curls up in these socks by the fireplace while reading a good book after a long day's work!

This post was all about parent trap costume amazon.

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