Not all movies get fashion right. Too many of them, unfortunately, leave us feeling bored and uninspired. But, once in every handful of films, we’re pleasantly surprised. And since 1998, and for the duration of 26 years later, The Parent Trap has been one of those movies–one that has become a constant source of inspiration and admiration for those within the fashion community.
They even say that every woman can be categorized as one of the five female characters. Let’s dive into the iconic fashion from The Parent Trap and you see which character you identify with the most.
Basically all of Elizabeth James’ Princess Diana-esque outfits
Most of us who grew up in the 90s and early 2000s might remember having the same love for both Elizabeth James and Princess Diana. Though, it might have taken years to pinpoint it. Like Diana, Elizabeth had a certain quality about her that made her so attractive, which seemed to be reflected in all of her outfits.
Her looks were never “loud” or over-the-top, yet everything she wore looked incredible. Elizabeth James didn’t have to try hard to be the center of attention. She just was. Timeless, classy, and chic, Elizabeth had a captivating air that made her irresistible. Steal Elizabeth’s style with similar pieces, here.
This look seemed to perfectly encapsulate the effortlessly chic aura of Elizabeth James.
At first glance, it would be easy to confuse this snapshot of the ever-chic Elizabeth for a candid picture of Princess Diana.
Another look that screamed Princess Diana–effortless, timeless, and classic.
We actually might have found the perfect dupes for Elizabeth’s shoes worn for this scene (tap image).
Meredith Blake might have been the Villian, but she was an iconically hot one
If you grew up on The Parent Trap, you can probably relate to feeling disgusted by Meredith but being equally in awe of her. It’s like car crash that you can’t look away from. She was mean, nasty, and calculating, but she was just as attractive and fashionable.
Every look of Meredith’s left our jaws on the floor. Here are some Meredith-inspired pieces.
The most unforgettable look of the movie. Meredith’s first look made it clear that she didn’t come to play–she came to win.
We’ll never forget Meredith’s hiking outfit. Formal wear or athletic clothes, you’ll never catch Meredith without a chic updo, jewelry, and accessories.
Meredith managed to make corporate office wear chic, attractive, and desirable.
Every classy girl needs a little black dress. Meredith paired hers with a long grey blazer.
Let’s not forget the Twins: Ever-chic Annie & Valley Cowgirl Hallie
In all of film history, I’m just not sure we’ve ever met two more fashionable eleven-year-olds. From camping to fancy dinners, poker nights to poolside lounging, Hallie and Annie had a memorable look for every occasion.
Steal the twins’ style with similar looks, here.
The twins stunned in their bright and yellow poolside looks after finally being reuinted post-switch.
Hallie and Annie pulled out their best ranch-style hiking fits for their camping trip with Cruella–erm, we mean, Meredith.
The twins looking casually chic in their matching polo shirts and headbands. Shop these shirts in our curated Parent Trap outfits list, here (or tap image).
Hallie’s pink Chinese dress worn for their boat dinner has specifically lived rent free in my head these past 26 years. For a similar one, tap image.
Next to Meredith’s poolside ensemble, Annie’s camp arrival outfit is probably the second most memorable one. And we might have found the most perfect set inspired by this look (tap image).
Even during meals at home, Annie was always dressed her best (Hallie as Annie in London).
Have you ever seen a better-dressed mum and daughter? We’ll wait.
Hallie proved just how cool she was to us viewers when she walked out in this ensemble for a game of poker.
As kids, we all wanted Hallie’s first-day-of-camp look. As adults? We still want it.
Annie as Hallie casually flexing in a Parker vineyard branded t-shirt. Click the image to get your own.
You Didn’t Think We Forgot Chessy Did You?
Chessy was like that cool aunt who preferred to be comfortable and casual, and yet always came out looking effortlessly hot. Whether she was cooking chili or helping around the ranch, her chic western style is one we continue to draw inspiration from.
Here are some pieces to steal Chessy’s style with.
THIS look specifically. That’s all.
How Chessy managed to look so comfortable yet so chic all the time, we’re still trying to figure out and replicate.
