Plaid, Pearls & Parent Traps: Fashion Forecasted by Twins. – Fashion in Film: The Parent Trap (1998)
Picture this: long-lost twins reuniting at summer camp in khakis, Keds, matching co-ords and dungarees, foreshadowing 25 years of rich-girlcore styling.
Photo: Pinterest
Before ‘clean girl’ and ‘old money’ aesthetics had hashtags, Hallie Parker and Annie James showed us how style communicates privilege, upbringing, belonging and class-coded performance. More than a ‘90s classic, The Parent Trap has become a case study in how fashion mirrors identity – and who gets to own which version of it.
Indeed, long before TikTok began categorizing women as ‘coastal granddaughters’ or ‘clean girls’, The Parent Trap gave us the blueprint:
Hallie Parker and Annie James weren’t just twins, they were opposing aesthetics of inherited affluence and style archetypes. Napa Valley vineyard countryside tomboy versus London prep-school legacy. And caught in the crossfire? One elegant, minimalist British wedding dress designer of a mother, one cozy housekeeper who basically invented Coastal Grandaughter chic, and one high-maintenance ‘ice queen.’
Let’s be clear: this wasn’t just a ‘90’s feel-good family film. It was a fashion thesis in disguise. A cinematic runway show on class-coded femininity. A couture case study on nature vs nurture through the lens of generational wealth and the role fashion plays in our lives.
Cue ‘Do You Believe in Magic,’ crack open some oreos with peanut butter and prepare to enter a world where an iconic handshake, a British accent and a Napa vineyard taught us everything we know about fashion lineage. It is time we dissect The Parent Trap not simply as a movie, but as a cultural fashion prophecy that still defines how we express (or obscure) wealth in 2025.
Spaces as Stylists: How Setting Shapes Aesthetics
In The Parent Trap, setting isn’t just backdrop, it is a moodboard. Both homes are visual indicators of taste and status, shaping how the twins dress and behave.
Annie’s London Townhouse: Georgian architecture, soft florals, and chinoiserie wallpaper. The house’s interior decor mirrors Annie’s wardrobe. It’s refined, traditional and untouched by expiring trends.
Hallie’s Napa Estate: open-plan, terracotta floors, rustic-meets-modern, big windows, sun-kissed, vineyard views and breeze-blown linen curtains. The rustic but aesthetic and beautiful decor mirrors Hallie’s style: free-spirited, fun, quirky but still iconic and curated.
A Look at The Twins - Fashion as Social DNA:
Photo: Pinterest
Hallie Parker – Trust-Fund Tomboy, California Coded:
Her look is casual, sun-kissed and effortlessly cool. She is laidback, sporty and slightly tomboy.
Wardrobe: Plaid flannels, Levi’s 501s, denim dungarees, chequered shorts and vintage oversized tees, short or braided hair, tangled bracelets, bandanas, and, of course, an outfit of hers isn’t complete without a pair of sunnies and her stuffed animal Cuppy. Don’t forget coloured nail polish. Casual and effortless is what Hallie strives for. Practical yet playful and stylish clothing reflects her active, outdoorsy lifestyle. She is the ultimate countryside girl giving country charm and vintage camp vibes.
Closet staple: faded Levi’s paired with a plaid flannel layered over a white ribbed tank and Converse.
What would Hallie Parker look like if she were to dress in 2025?
Hallie would definitely be rocking some colourful Sambas and a baseball cap, as well as vintage Levi’s and Miu Miu oval leopard sunglasses. She would definitely love the headscarf trend.
Think: Emma Chamberlain’s Napa-girl chic.
Photo: Pinterest
Annie James – London Old Money:
Meanwhile, Annie – raised in a Georgian London townhouse with a monogrammed bathrobe – offers a different fashion thesis.
Wardrobe: Monogrammed pajamas, matching and elegant co-ords, pleated skirts, headbands (it’s giving Blair Waldorf), knee socks, ballet flats and bows. She is polished, preppy, and understatedly expensive.
How would Annie James dress in 2025?
Think Max Mara, Sézane and Ralph Lauren. She is into understated handbags, cashmere sweaters and owns vintage Hermes scarves. She is definitely into the scarf trend but she uses the foulard as a handbag accessory or around her neck, not as a bandana in the free-spirit way Hallie does. Annie is legacy coded.
Photo: Pinterest
Elizabeth James – The Mother, the Myth, the Minimalist
She is the eternal icon of understated elegance. As Hallie Parker said, and spoke for all of us, ‘my mom is too cool.’ Played by Natasha Richardson, Elizabeth James is the template for the modern luxury minimalist. She doesn't need logos, her presence is enough.
Her look? Cream-toned silk blouses, tailored trousers, a long coat and a neutral lip.
Her signature 90s looks:
High-waisted trousers with silk button downs
Cream-toned suit jackets
Slinky, boat-neck little black dress
Gold watch and no flashy accessories
Simple but luxurious earrings, like pearls
Crisp white shirts
Her famous Ralph light blue oversized shirt outfit in which she tells the girls she won’t be joining the annual Camping trip
Her vintage looks in todays fashion:
She would wear The Row, Toteme, Loro Piana and Phoebe Philo. Elizabeth manages to look powerful and emotionally composed through simplicity. She would smell like Federic Malle. Her entire wardrobe would fit in two garment bags and somehow feel more powerful than any influencer’s walk-in closet.
Every cool mum owes her a thank-you note.
Photo: Pinterest
Meredith Blake – The Gold-Digger Rebrand is Complete
In 1998, Meredith was the villain: chasing Nicholas Parker’s money. But in 2025, she’s been reclaimed. She has undergone a full cultural rebrand. We now see her for what she was: a driven 26-year-old determined to secure her spot in a male-dominated, wealth-gated world monopolising and manipulating people through her fashion looks.
Meredith wasn’t born rich, she fashioned herself rich. She was aspirational and manipulative. And in 2025? She’d be a luxury lifestyle Youtuber and a Range Rover mum with an Iced latte always in hand and a pilates fit on the go.
Wardrobe: oversized square sunglasses, sharp pencil skirts, gold hoop earrings and her staple, daring matte red lipstick.
Her look now:
Versace Resort, Ferragamo kitten heels and sleek swimsuits from Eres and Marysia. Think Sofia Richie’s Monaco wardrobe, but with a little more spice.
Meredith is no longer the antagonist, she’s the aspirational anti-hero. She uses fashion to climb and achieve what she wants.
Photo: Pinterest
Chessy: The Coastal Grandma
Let’s not forget Chessy: loyal, warm, and owning that relaxed, effortlessly cool look.
Her style? Loose button-downs, linen pants, and bandanas. She has started the Coastal Granddaughter trend and she doesn’t even know it.
Today she would shop at Eileen Fisher, Jenni Kayne, Doen and Apiece Apart.
She represents comfort and timeless practicality. Chessy doesn’t dress for the male gaze, she dresses for herself. Her cozy fashion choices are a reflection of her emotional resonance.
Which character are you based on your Parent Trap fashion aesthetic?
Photo: Pinterest
Elizabeth James: If you have the old money aura about you, you wear navy and understated, neutral colours with such elegance, and you don’t dress boldly and over-the-top but always end up being the most charming and admired person in the room, then Elizabeth is for you.
Hallie Parker: If you’re a thrifting queen, own multiple pairs of dad sneakers, have a ridiculous amount of charm-bracelets, live in oversized flannel shirts and Levi’s, then Hallie is you and you are her.
Annie James: If you have a capsule wardrobe, your tote bags are monogrammed, you wear matching pleated co-ords and headbands, and you never leave the house without a trenchcoat, then Annie is just the one for you.
Meredith Blake: If you are hyper-styled, unapologetically high-maintenance, have daring energy and when people call you a bitch, you consider it branding, and you bring drama and designer energy into every room, then Meredith is your style icon.
Chessy: If you prioritise comfort over trends, own endless amounts of oversized button-downs and probably smell like fig and lavender then Chessy is your fashion inspiration.
In a time where style is more performative than ever and the latest trends expire faster than a Rhode peptide lip treatment sells out, The Parent Trap still holds the blueprint. Its’ women remind us that fashion isn’t just about taste - it’s about lineage, origin and belonging.
So, whether you are team Annie, Hallie, Meredith, Chessy or the eternally elegant Princess Diana-coded Elizabeth James, just know that boring isn’t an option. Whatever your aesthetic, own it. The Fashion Stock Market is always keeping tabs.
XOXO, The Fashion Stock Market
Cover Photo: Pinterest
Editor: Felicity Field
